Facile Synthesis of Flavonoid 7-O-Glycosides

Size: px
Start display at page:

Download "Facile Synthesis of Flavonoid 7-O-Glycosides"

Transcription

1 Facile Synthesis of Flavonoid 7-O-Glycosides Ming Li, a Xiuwen Han, a Biao Yu b * a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian , China b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai , China. Fax: (86) , Supporting Information Experimental 1. General remarks. Solvents were distilled from the appropriate drying agents before use. Unless stated otherwise, all reactions were monitored by TLC on silica gel HF 254 (0.5 mm, Qingdao, China). Spots were detected under UV light or by charging with 10% H 2 SO 4 in MeOH. Flash column chromatography was carried out on silica gel H (400 mesh, Qingdao, China). Optical rotations were measured on a Perkin-Elmer 241 MC polarimeter. 1 H NMR spectra were recorded on a Bruker AM-300 spectrometer using tetramethylsilane as an internal reference. Mass spectra were recorded on a HP5989A mass spectrometer. Elemental analyses were performed on a Perkin-Elmer Model 2400 instrument. 2. General procedure for acylation of flavonoids 2.1 4, 7, 8-Trihexanoxy isoflavone (4) Method A: To a solution of 4, 7, 8-trihydroxy isoflavone (1.08 g, 4.00 mmol) in pyridine (10 ml) and CHCl 3 (5 ml) was added DMAP (155 mg, 1.27 mmol, 0.3 equiv.) and hexanoyl chloride (3.2 ml, mmol, 5.7 equiv.) at -20 o Cintwo portions. After stirring for 9 h, the mixture was diluted with CH 2 Cl 2, and washed with 1 M aq. HCl and saturated brine subsequently. The organic phase was dried over anhydrous Na 2 SO 4 and then concentrated. The residue was applied to a silica gel column chromatography (petroleum ether-etoac, 9:1) to afford 4 as a white solid (1.97 g, 87%): 1 H NMR (300 MHz, CDCl 3 ): 8.19 (d, 1 H, J = 9.0 Hz), 7.96 (s, 1 H),

2 (d, 2 H, J = 8.4 Hz), 7.25 (d, 1 H, J = 8.7 Hz), 7.16 (d, 2 H, J = 8.4 Hz), 2.67 (t, 2 H, J = 7.8 Hz), (m, 4 H), (m, 6 H), (m, 12 H), (m, 9 H). 13 CNMR(75MHz,CDCl 3 ): , , , , , , , , , , , , , , , 34.35, 33.97, 33.64, 31.18, 24.58, 24.50, 22.24, EI-MS (m/z): 466, 368, 270, 99, 71. Anal. Calcd for C 33 H 40 O 8 : C, 70.19%, H, 7.14%; Found: C, 70.10%, H, 7.24%. 2.2 Chrysin benzoate (6c) Method B: To a solution of Chrisin (1.00 g, 3.93 mmol) in anhydrous pyridine (7 ml), benzoyl chloride (1 ml) was added at 0 o C. After stirring at 60 o C for 7 h, TLC showed that the reaction was completed. The mixture was quenched with methanol and then concentrated and diluted with CH 2 Cl 2. The organic phase, after washing with 1N aq. HCl and saturated brine sequentially, was dried over anhydrous Na 2 SO 4 and concentrated. The residue was crystallized in petroleum ether-etoac (1:2) to produce 6c as a white solid (1.23 g, 95%). 1 H NMR (300 MHz, CHCl 3 ): 8.29 (d, 2 H, J =7.4 Hz), 8.23 (d, 2 H, J = 7.4 Hz), 7.89 (dd, 2 H, J = 2.2, 7.0 Hz), (m, 10 H), 7.15 (d, 1 H, J = 2.2 Hz), 6.66 (s, 1 H). EI-MS (m/z): 463 (M + H + ), 105, 77. Anal. Calcd for C 29 H 18 O H 2 O: C, 74.59%, H, 3.99%; Found: C, 74.85%, H, 3.72%. 2.3 Chrysin hexanoate (6a) Method B was used to provide 6c (87%) as a white powder: 1 H NMR (300 MHz, CDCl 3 ): (m, 2 H), (m, 3 H), 7.35 (d, 1 H, J = 2.2 Hz), 6.83 (d, 1 H, J = 2.0 Hz), 6.66 (s, 1 H), 2.74 (t, 2 H, J = 7.7 Hz), 2.60 (t, 2 H, J = 7.5 Hz), (m, 4 H), (m, 8 H), (m, 6 H). EI-MS (m/z): 352, 254. Anal. Calcd for C 27 H 30 O 6 : C, 71.98%, H, 6.71%; Found: C 72.00%, H, 6.89%. 2.4 Chrysin acetate (6b) Ref Daidzein hexanoate (8a) 2

3 Method A was used to prepare 8c (77%) as a white solid from daidzein. 1 H NMR (300 MHz, CDCl 3 ): 8.33 (d, 1 H, J = 8.8 Hz), 8.02 (s, 1 H), 7.59 (d, 2 H, J = 8.8 Hz), 7.31 (d, 1 H, J = 2.2 Hz), (m, 3 H), 2.62 (t, 2 H, J = 7.4 Hz), 2.58 (t, 2 H, J =7.7 Hz), (m, 2 H), (m, 8 H), (m, 6 H). EI-MS (m/z): 451 [M +H + ], 352, 353, 254, 99, 77. Anal. Calcd for C 27 H 30 O 6 : C, 71.98%, H, 6.71%; Found: C 72.17%, H, 6.97%. 2.6 Daidzein acetate (8b) Ref Quercetin acetate (10a) Ref.: Picq, M.; Prigent, A. F.; Némoz, G.; André, A. C.; Pacheco, H. J. Med. Chem. 1982, 25, Quercetin benzoate (10b) Method B was used to prepare 10b (56%) as a white solid: 1 H NMR (300 MHz, DMSO-d 6 ): (m, 30 H). EI-MS (m/z): 823 (M + H + ), 105, 77. Anal. Calcd for C 50 H 30 O 12 : C, 72.99%, H, 3.68%; Found: C 73.16%, H, 3.57% ,8-Dihexanoxy chromone (14). Method A was used to prepare 14 (85%) as an orange syrup: 1 H NMR (300 MHz, CDCl 3 ): 8.10 (d, 1 H, J = 9.0 Hz), 7.80 (d, 1 H, J = 6.3 Hz), 7.23 (d, 1 H, J =9.0Hz), 6.34 (d, 1 H, J = 6.3 Hz), 2.65 (t, 2 H, J = 7.2 Hz), 2.58 (t, 2 H, J = 7.5 Hz), (m, 4 H), (m, 8 H), (m, 6 H); EI-MS (m/z): 375, 276, 178, 99, 71, 43. Anal. Calcd for C 21 H 26 O 6 : C, 67.36%, H, 7.00%; Found: C 66.94%, H, 7.30%. 3. Preparation of 7,8-dihexanoxyisoflavone 4 -O- 2, 3, 5 -tri-o-benzoyl- -Darabinofuranoside (12) 3.1 7, 8-Dihexanoxy-4 -hydoxy isoflavone (28) To a solution of 4, 7, 8-trihydroxy isoflavone (806 mg, 2.98 mmol) in pyridine (8 ml) and CHCl 3 (4 ml) at -78 o C was added DMAP (93 mg, 0.76 mmol, 0.26 equiv.) and 3

4 hexanoyl chloride (0.9 ml, 6.44 mmol, 2.16 equiv.). The mixture was warmed to 0 o C in a period of 10 h, and then diluted with CH 2 Cl 2. The organic phase, after washing with 1 M aq. HCl and saturated brine subsequently, was dried over anhydrous Na 2 SO 4 and then concentrated. The residue was applied to a silica gel column chromatography (petroleum ether-etoac, 3:1) to afford 28 as a white solid (1.06 g, 76%): 1 H NMR (300 MHz, DMSO-d 6 ): 9.64 (s, 1 H), 8.46 (s, 1 H), 8.08 (d, 1 H, J = 8.7 Hz), 7.46 (d, 1 H, J = 8.7 Hz), 7.42 (d, 2 H, J = 8.4 Hz), 6.85 (d, 2 H, J = 8.4 Hz), 2.72 (t, 2 H, J =7.5 Hz), 2.66 (t, 2 H, J = 7.5 Hz), (m, 4 H), (m, 8 H), (m, 6 H). 13 CNMR(75MHz,CDCl 3 ): , , , , , , , , , , , , , , , 33.97, 33.66, 31.17, 24.58, 24.49, 22.23, ESI-MS (m/z): [M + Na + ], [M + H + ]. Anal. Calcd for C 27 H 30 O 7 0.5H 2 O: C, 68.19%, H, 6.57%; Found: C 68.56%, H, 6.54% ,8-Dihexanoxyisoflavone 4 -O- 2, 3, 6 -tri-o-benzoyl- -D-arabinofuranoside (12) See the general procedure for the glycosylation (Section 6). The coupling of 28 with 18 produced 12 in 88% yield as a foam: [ ] 20 D = 34.1 (c 1.04, CHCl 3 ); 1 H NMR (300 MHz, CDCl 3 ): 8.21 (d, 1 H, J = 8. 8 Hz), (m, 2 H), (m, 4 H), 7.96 (s, 1 H), (m, 14 H), 6.04 (brs, 1 H), 5.83 (brs, 1 H), 5.72 (d, 1 H, J =3.3 Hz), (m, 3 H), 2.68 (t, 2 H, J = 7.4 Hz), 2.61 (t, 2 H, J = 7.7 Hz), (m, 4 H), (m, 8 H), (m, 6 H). 13 CNMR(75MHz,CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , , , , , 82.19, 82.10, 77.68, 63.64, 33.99, 33.67, 31.18, 24.61, 24.52, 22.26, EI-MS (m/z): 445, 368, 270, 105, 77, 71, 43. Anal. Calcd for C 53 H 50 O 14 : C, 69.88%, H, 5.53%; Found: C, 69.84%, H, 5.48%. 4. General procedure for the regioselective deacylation To a solution of the flavonoid ester (1 mmol) in anhydrous NMP at 0 o Cwasadded imidazole (0.35 equiv.) followed by PhSH (1.2 molar equiv.). After stirring at 25 o C until the disappearance of the starting material as monitored by TLC, the mixture was 4

5 diluted with CH 2 Cl 2, and then washed with 1 N aq. HCl and saturated brine subsequently. The organic phase was dried over anhydrous Na 2 SO 4 and concentrated. The residue was applied to a silica gel column chromatography to afford the product , 8-Dihexanoxy-7-hydroxy isoflavone (5) Compound 5 was obtained as a white solid: 1 H NMR (300 MHz, DMSO-d 6 ): (s,1h),8.42(s,1h),7.87(d,1h,j = 9.3 Hz), 7.58 (d, 2 H, J = 8.7 Hz), (m,3h),2.67(t,2h,j = 7.4 Hz), 2.57 (t, 2 H, J = 7.4 Hz), (m, 4 H), (m, 8 H), (m, 6 H); 13 C NMR (75 MHz, DMSO-d 6 ): , , , , , , , , , , , , , , 33.62, 33.16, 30.78, 30.68, 24.31, 24.19, 21.94, 13.96; ESI-MS (m/z): [M + H + ]. Anal. Calcd for C 27 H 30 O 7 : C, 69.51%, H, 6.48%; Found: C 69.49%, H, 6.57%. Phenylthiohexanoate was isolated as a liquid: 1 H NMR (300 MHz, CDCl 3 ): 7.42 (m, 5 H), 2.66 (t, 2 H, J = 7.2 Hz), 1.57 (m, 2 H), 1.36 (m, 4 H), 0.91 (t, 3 H, J =6.9Hz); EI-MS (m/z): 208 (M + ), 109, 99, 71, 43. Anal. Calcd for C 12 H 16 OS: C, 69.11%, H, 7.74%, S 15.39%; Found: C 68.90%, H, 7.70%, S 15.06% O-Hexanoyl chrysin (7a) Compound 7a was obtained as a white powder: 1 H NMR (300 MHz, DMSO-d 6 ): (s, 1 H), 8.03 (m, 2 H), 7.58 (m, 3 H), 6.94 (d, 1 H, J = 2.2 Hz), 6.77 (s, 1 H), 6.55 (d, 1 H, J = 2.5 Hz), 2.62 (t, 2 H, J = 7.4 Hz), 1.67 (m, 2 H), 1.36 (m, 4 H), 0.94 (t, 3 H, J =7.0Hz).ESI-MS(m/z): [M + H + ]. Anal. Calcd for C 21 H 20 O 5 :C, 71.58%, H, 5.72%; Found: C 71.49%, H, 5.83% O-Acetyl chrysin (7b) Ref O-Benzoyl chrysin (7c) 5

6 Compound 7c was obtained as a white powder: 1 H NMR (300 MHz, DMSO-d 6 ): (s, 1 H), (m, 4 H), (m, 6 H), 7.01 (m, 1 H), 6.74 (m, 1 H), 6.70 (s, 1 H). ESI-MS: [M + Na + ], [M + H + ]. Anal. Calcd for C 22 H 14 O 5 :C, 73.74%, H, 3.94%; Found: C 73.30%, H, 3.97% O-Hexanoyl daidzein (9a) Compound 9a was obtained as a white solid: 1 H NMR (300 MHz, DMSO-d 6 ): (s,1h),8.42(s,1h),7.99(d,1h,j = 8.8 Hz), 7.61 (d, 2 H, J = 8.5 Hz), 7.17 (d, 2 H, J = 8.5 Hz), (m, 2 H), 2.59 (t, 2 H, J = 7.4 Hz), (m, 2 H), (m,4h),0.90(t,3h,j =6.6Hz);ESI-MS(m/z): [M + H + ]. Anal. Calcd for C 21 H 20 O H 2 O C, 70.67%, H, 5.79%; Found: C 70.91%, H, 5.78% O-acetyl daidzein (9b) Ref.: , 3, 4, 5-Tetra-O-acetyl quercetin (11a) Ref.: Natoli, M.; Nicolosi, G.; Piattelli, M. J. Org. Chem. 1992, 57, , 3, 4, 5-Tetra-O-benzoyl quercetin (11b) Compound 11b was obtained as a white solid: 1 H NMR (300 MHz, DMSO-d 6 ): (s,1h),8.19(d,1h,j = 1.8 Hz), 8.11 (d, 4 H, J = 7.2 Hz), (m, 5 H), (m, 13 H), 7.08 (d, 1 H, J = 2.1 Hz), 6.86 (d, 1 H, J =2.4Hz). 13 CNMR(75MHz, DMSO-d 6 ): , , , , , , , , , , , , , , , , , , , , , , , , , , , ESI-MS (m/z): [M + H + ]. Anal. Calcd for C 43 H 26 O H 2 O: C, 70.97%, H, 3.74%; Found: C 70.95%, H, 3.43% Hexanoxy-7-hydroxy isoflavone 4 -O-2, 3, 5 -tri-o-benzoyl- -Darabinofuranoside (13) 6

7 Compound 13 was obtained as a semi-solid: 1 H NMR (300MHz, DMSO-d 6 ): (s, 1 H), 8.37 (s, 1 H), (m, 6 H), 7.88 (d, 1 H, J = 9.0 Hz), (m, 9 H),7.37(d,2H,J = 7.8 Hz), 7.24 (d, 1 H, J = 8.1 Hz), 7.10 (d, 1 H, J = 9.3 Hz), 6.32 (brs, 1 H), 5.68 (m, 2 H), 4.71 (m, 3 H), 2.66 (t, 2 H, J = 7.2 Hz), (m, 2 H), (m, 4 H), 0.87 (t, 3 H, J =7.2Hz).ESI-MS(m/z): [M + H + ]. Anal. Calcd for: C 47 H 40 O H 2 O: C, 68.69%, H, 5.03%; Found: C 68.61%, H, 5.34% Hexanoxy-7-hydroxy chromone (15) Compound 15 was obtained as a yellow solid: 1 H NMR (300 MHz, DMSO-d 6 ): (s,1h),8.17(d,1h,j = 6.3 Hz), 7.77 (d, 2 H, J = 9.3 Hz), 7.07 (d, 1 H, J =9.0Hz), 6.26 (d, 1 H, J = 6.3 Hz), 2.68 (t, 2 H, J = 7.4 Hz), (m, 2 H), (m, 4 H),0.90(m,3H).ESI-MS(m/z): [M + H + ]. Anal. Calcd for C 15 H 16 O 5 :C, 65.21%, H, 5.84%; Found: C 65.23%, H, 5.82% ,3,4,6-Tetra-O-benzoyl-D-glucopyranosyl (N-phenyl)trifluoroacetimidate (16) Ref. 20b 5.2 2,3,4-Tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)trifluoroacetimidate (17) Ref. 20b 5.3 2,3,5-Tri-O-benzoyl-D-arabinofuranosyl (N-phenyl)trifluoroacetimidate (18) Compound 18 (939 mg, 92%) was prepared as a white foam from 2,3,5-tri-O-benzoyl- D-arabinofuranoside using the procedure described in ref. 20b. Several mg of the pure -isomer was obtained for characterization: [ ] 20 D = (c 1.40, CHCl 3 ). 1 HNMR (300 MHz, CDCl 3 ): (m, 6 H), (m, 11 H), 7.09 (t, 1 H, J =7.5 Hz), 6.88 (d, 2 H, J = 7.5 Hz), 6.65 (brs, 1 H), 5.81 (brs, 1 H), 5.68 (d, 1 H, J =2.7 Hz), (m, 3 H). Anal. Calcd for C 34 H 26 NO 8 F 3 :C,64.46%,H,4.14%,N, 2.21%; Found: C 64.29%, H, 4.10%, N, 2.40%. 6 General procedure for glycosylation 7

8 To a suspension of the flavonoid acceptor (0.1 mmol), glycosyl trifluoroacetimidate donor (0.25 mmol), and 4Å molecular sieves in CH 2 Cl 2 (5mL)wasaddedasolutionof BF 3 Et 2 OinCH 2 Cl 2 (0.1 M 0.3 ml). After stirring at room temperature overnight, the reaction was quenched with Et 3 N. The mixture was then filtrated and concentrated. The residue was purified on a silica gel column chromatography to give the glycoside , 8-Dihexanoxyisoflavone 7-O-2,3,4,6 -tetra-o-benzoyl- -D-glucopyranoside (19) Compound 19 was obtained as a white foam: [ ] 20 D =23.3 (c 1.06, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): (m, 10 H), (m, 15 H), 7.14 (d, 2 H, J =8.4 Hz), 6.02 (t, 1 H, J = 9.6 Hz), 5.87 (dd, 1 H, J = 7.8, 9.3 Hz), 5.70 (t, 1 H, J =9.6Hz), 5.52 (d, 1 H, J =7.2 Hz), 4.73 (dd, 1 H, J = 2.4, 9.9 Hz), 4.53 (dd, 1 H, J = 6.9, 12.0 Hz), 4.41 (m, 1 H), (m, 4 H), (m, 4 H), (m, 8 H), (m, 6 H). 13 CNMR(75MHz,CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , , , , , , , 99.08, 73.01, 72.54, 71.31, 69.35, 62.96, 34.34, 33.20, 31.21, 31.15, 24.56, 24.20, 22.27, EI-MS (m/z): 466, 368, 270, 105, 99, 77, 71, 43. Anal. Calcd for: C 61 H 56 O 16 C, 70.11%, H, 5.40%; Found: C 69.74%, H, 5.52% , 7-Dihexanoxyisoflavone 8-O-2,3,4,6 -tetra-o-benzoyl- -D-glucopyranoside (19a) Compound 19a was obtained as a white foam: [ ] 20 D =1.2(c 1.15, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): (m, 9 H), (m, 15 H), 7.14 (d, 2 H, J =8.4 Hz), 7.10 (d, 1 H, J = 9.0 Hz), 6.02 (t, 1 H, J = 9.6 Hz), (m, 2 H), 5.37 (d, 1 H, J = 7.5 Hz), 4.53 (m, 2 H), 4.11 (m, 1 H), (m, 4 H), (m, 2 H), (m, 2 H), (m, 4 H), (m, 4 H), 0.95 (t, 3 H, J =6.6Hz), 0.89 (t, 3 H, J =6.9Hz). 13 C NMR (75 MHz, CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , , 8

9 121.65, , , , 72.68, 72.20, 69.02, 34.38, 33.91, 31.26, 31.11, 24.61, 24.28, 22.30, Anal. Calcd for C 61 H 56 O 16 : C, 70.11%, H, 5.40%; Found: C, 69.83%, H, 5.69% , 8-Dihexanoxyisoflavone 7-O-2,3,4 -tri-o-acetyl- -L-rhamnopyranoside (20) Compound 20 was obtained as a white foam: [ ] 20 D =-64.1(c 1.18, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): 8.14 (d, 1 H, J = 8.1 Hz), 7.95 (s, 1 H), 7.55 (d, 2 H, J =8.4Hz), 7.30 (d, 1 H, J = 8.1 Hz), 7.15 (d, 2 H, J = 8.4 Hz), 5.60 (brs, 1 H), 5.44 (m, 1 H), 5.37 (dd, 1 H, J =3.0,10.2Hz),5.17(t,1H,J = 9.9 Hz), 2.81 (t, 2 H, J = 7.4 Hz), 2.57 (t, 2 H, J = 7.5 Hz), 2.20 (s, 3 H), 2.07 (s, 3 H), 2.02 (s, 3 H), (m, 4 H), 1.41 (m, 8 H), 1.21(t,3H,J = 6.0 Hz), 0.93 (m, 3 H). 13 C NMR (75 MHz, CDCl 3 ): , , , , , , , , , , , , , , , , , 95.91, 70.20, , 68.06, 34.34, 33.41, 31.15, 24.58, 24.41, 22.27, 20.72, 20.60, 17.35, EI-MS (m/z): 467, 368, 273, 153, 111, 99, 71, 43. Anal. Calcd for C 39 H 46 O 14 :C,63.41%,H,6.28%; Found: C, 63.15%, H, 6.48% , 8-Dihexanoxyisoflavone 7-O-2,3,5 -tri-o-benzoyl- -D-arabinofuranoside (21) Compound 21 was obtained as a white foam: [ ] 20 D = 34.5 (c 0.91, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): 8.19 (d, 1 H, J = 8.1 Hz), 8.12 (m, 2 H), (m, 4 H), 7.95 (s, 1 H), (m, 12 H), 7.17 (d, 2 H, J = 8.7 Hz), 6.09 (brs, 1 H), 5.82 (brs, 1 H), 5.72 (d, 1 H, J = 3.3 Hz), (m, 3 H), (m, 4 H), (m, 4 H), (m, 4 H), (m, 4 H), (m, 6 H); 13 CNMR(75MHz, CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , , , 82.68, 81.99, 63.30, 34.35, 33.64, 31.21, 31.12, 24.61, 24.20, 22.26, 22.15, EI-MS (m/z): 466, 445, 368, 270, 105, 99, 77, 71, 43. Anal. Calcd for C 53 H 50 O 14 : C, 69.88%, H, 5.53%; Found: C, 69.60%, H, 5.53%. 9

10 , 7-Dihexanoxyisoflavone 8-O-2,3,5 -tri-o-benzoyl- -D-arabinofuranoside (21a) Compound 21a was obtained as a white foam: [ ] 20 D = 18.3 (c 0.95, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): (m, 3 H), (m, 4 H), 7.93 (s, 1 H), (m, 14 H), 5.60 (brs, 1 H), 5.44 (brs, 1 H), 5.71 (d, 1 H, J = 3.7 Hz), 5.08 (m, 1 H), 4.90 (dd, 1 H, J = 3.6, 12.1 Hz), 4.72 (dd, 1 H, J = 5.8, 11.8 Hz), (m, 4 H), (m, 4 H), (m, 8 H), (m, 6 H); 13 CNMR(75MHz, CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , , , , , , 82.96, 81.99, 77.70, 63.84, 34.34, 33.84, 31.21, 31.09, 24.55, 24.26, 22.23, 22.15, 13.82, 13.76; EI-MS (m/z): 445, 368, 270, 105, 99, 77, 43. Anal. Calcd for C 53 H 50 O 14 : C, 69.88%, H, 5.53%; Found: C, 69.63%, H, 5.80% O-Hexanoyl daidzein 7-O-2,3,4,6 -tetra-o-benzoyl- -D-glucopyranoside (22) Compound 22 was obtained as a white foam: [ ] 20 D = 15.8 (c 0.93, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): 8.11 (d, 1 H, J = 9.6 Hz), (m, 8 H), 7.81 (s, 1 H), (m, 14 H), 7.16 (d, 2 H, J = 8.5 Hz), (m, 2 H), 6.04 (t, 1 H, J =9.2Hz), 5.85 (dd, 1 H, J = 7.4, 9.3 Hz), 5.74 (t, 1 H, J = 9.3 Hz), 5.60 (d, 1 H, J =7.4 Hz), 4.73 (dd, 1H, J = 2.4, 9.9 Hz), 4.53 (dd, 1 H, J = 6.9, 12.0 Hz), 4.41 (m, 1 H), 2.57 (t, 2 H, J = 7.6 Hz), 1.77 (m, 2 H), 1.40 (m, 4 H), 0.94 (t, 3 H, J =6.9Hz). 13 CNMR(75MHz, CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , , , , , , , 98.60, 73.01, 72.53, 71.48, 69.34, 63.07, 34.35, 31.24, 24.59, 22.29, EI-MS (m/z): 579, 352, 254, 105, 77, 71, 43. Anal. Calcd for C 55 H 40 O 14 : C, 70.96%, H, 4.98%; Found: C, 71.00%, H, 5.34% O-Hexanoyl daidzein 7-O-2,3,5 -tri-o-benzoyl- -D-arabinofuranoside (23) 10

11 Compound 23 was obtained as a white foam: [ ] 20 D = 48.6 (c 1.19, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): 8.26 (d, 1 H, J = 9.6 Hz), (m, 6 H), 7.97 (s, 1 H), (m, 11 H), 7.24 (dd, 2 H, J = 1.5, 11.1 Hz), (m, 3 H), 6.09 (brs, 1 H), 5.84 (brs, 1 H), 5.73 (d, 1 H, J = 3.9 Hz), 4.83 (dd, 1 H, J = 5.4, 8.1 Hz), (m, 2 H), 2.57 (t, 2 H, J = 7.5 Hz), (m, 2 H), (m, 4 H), 0.93 (t, 3 H, J = 6.9 Hz). 13 C NMR (75 MHz, CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , 82.77, 81.95, 63.42, 34.37, 31.24, 24.59, 22.29, EI-MS (m/z): 445, 253, 105, 77, 43. Anal. Calcd for C 47 H 40 O 12 : C, 70.85%, H, 5.06%; Found: C 70.80%, H, 4.89% ,3,4,5-Tetra-O-acetyl quercetin 7-O-2,3,4,6 -tetra-o-benzoyl- -Dglucopyranoside (24) Compound 24 was obtained as a white solid: [ ] 20 D = 23.9 (c 1.26, CHCl 3 ); 1 HNMR (300 MHz, CDCl 3 ): (m, 8 H), (m, 15 H), 6.99 (d, 1 H, J =2.4 Hz), 6.75 (d, 1 H, J = 2.7 Hz), 6.02 (t, 1 H, J = 9.3 Hz), 5.85 (dd, 1 H, J = 7.5, 9.0 Hz), 5.75 (t, 1 H, J = 9.0 Hz), 5.62 (d, 1 H, J = 7.5 Hz), 4.78 (m, 1 H), 4.49 (m, 2 H), 2.36 (s,3h),2.35(s,3h),2.34(s,6h). 13 CNMR(75MHz,CDCl 3 ): , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 98.20, 73.02, 72.39, 71.28, 69.20, 20.95, 20.60, EI-MS (m/z): 470, 428, 386, 344, 302, 105, 77, 43. Anal. Calcd for C 57 H 44 O 20 H 2 O: C, 64.16%, H, 4.34%; Found: C, 64.30%, H, 4.30%. 7. General procedure for the deprotection of isoflavone glycosides The isoflavone ester (0.1 mmol) was dissolved in methanol-thf (4 ml, 1:1) followed by addition of K 2 CO 3 (2.2 equiv.) in H 2 O (0.3 ml). After stirring for 4 h at 40 o C, the mixture was neutralized with Dowex-50 H +, and then filtrated and concentrated. The 11

12 residue was purified by a silica gel column chromatography to afford the corresponding isoflavone glycoside ,8-Dihydroxy isoflavone 7-O- -D-arabinofuranoside (1) Compound 1 was obtained as a white solid: [ ] D = (c 1.12, MeOH), Lit. [ ] D = 125 (c 0.12, DMSO) (Ref. 3a); 1 H NMR (300 MHz, CD 3 OD-CDCl 3, 1:1): 8.15 (s, 1 H),7.73(d,1H,J = 9.0 Hz), 7.40 (d, 2 H, J = 8.1 Hz), 7.33 (d, 1 H, J = 9.0 Hz), 6.91 (d, 2 H, J = 8.1 Hz), 5.79 (brs, 1 H), 4.40 (brs, 1 H), 4.27 (m, 1 H), 4.18 (d, 1 H, J =3.6 Hz), 3.82 (dd, 1 H, J = 4.2, 11.7 Hz), 3.75 (dd, 1 H, J = 2.7, 12.0 Hz). 13 CNMR(75 MHz, DMSO-d 6 ): , , , , , , , , , , , , , 86.06, 81.57, 76.84, ESI-MS (m/z): [M + H + ]. 7.2 Daidzein 7-O- -D-glucopyranoside (2) Compound 2 was obtained as a white solid: [ ] 14 D = (c 0.29, DMF); Lit. [ ] 24 D = (c 0.001, DMSO) (Ref.: Lewis P.; Kaltia, S.; Wähälä, K. J. Chem. Soc. Perkin Trans. 1, 1998, 2481); 1 H NMR (300MHz, DMSO-d 6 ): 9.54 (brs, 1 H), 8.38 (s, 1 H), 8.03 (d, 1 H, J = 9.0 Hz), 7.39 (d, 2 H, J = 8.1 Hz), 7.22 (d, 2 H, J = 1.5 Hz), 7.13 (dd, 1H,J = 1.5, 9.0 Hz), 6.80 (d, 2 H, J = 8.1 Hz), 5.43 (d, 1 H, J = 2.4 Hz), 5.14 (d, 1 H, J =2.4Hz),5.08(m,2H),4.60(m,1H),4.08(m,1H),3.45(m,2H). 13 CNMR(75 MHz, DMSO-d 6 ): , , , , , , , , , , , , , , 77.38, 76.66, 73.32, 69.83, ESI-MS (m/z): [M + Na + ], [M + H + ]. 7.3 Quercetin 7-O- -D-glucopyranoside (3) To a solution of 24 (145 mg, 0.14 mmol) in CHCl 3 (3mL)wasaddedasolutionof NaOMe in methanol (1 N, 5 ml) in one portion at argon atmosphere. The reaction was completed as shown by TLC after stirring at 6 o C for 4 h. The mixture was neutralized by Dowex-50 H + resin, and then filtrated. The organic phase was concentrated to give a residue, which was purified by a Sephadex LH-20 gel column (MeOH-H 2 O, 74:26) to 12

13 produce 3 as a yellow powder (32 mg, 50%): [ ] 14 D = (c 0.26,MeOH),Lit. [ ] 20 D =-59(Ref.:Shelyuto,V.L.;Bondarenko,V.G.;Chem. Nat. Compd. 1985, 21, 534); 1 H NMR (300 MHz, DMSO-d 6 ): (s, 1 H), 9.50 (brs, 3 H), 7.72 (d, 1 H, J = 2.2 Hz), 7.55 (d, 1 H, J = 8.8 Hz), 6.90 (d, 1 H, J = 8.5 Hz), 6.76 (d, 1H, J =1.9Hz), 6.42 (d, 1 H, J = 1.7 Hz), 5.19 (brs, 1 H), 5.07 (d, 1 H, J = 7.1 Hz), 5.09 (brs, 2 H), 4.60 (brs, 1 H), 3.70 (m, 2 H), (m, 4 H). 13 C NMR (75 MHz, DMSO-d 6 ): , , , , , , , , , , , , , 98.96, 94.49, 77.35, 76.56, 73.32, 69.75, ESI-MS (m/z): [M + H + ] , 8-Dihydroxyisoflavone 7-O- -D-glucopyranoside (25) Compound 25 was obtained as a white foam: [ ] D =-20.8(c 0.17, DMF), Lit. [ ] D = (c 0.55, MeOH)(Ref.3b); 1 H NMR (300 MHz, DMSO-d 6 ): 9.55 (brs, 1 H), 8.39 (s, 1 H), 7.80 (d, 2 H, J = 8.4 Hz), 7.49 (d, 1 H, J = 9.3 Hz), 7.39 (d, 2 H, J =8.4 Hz), 7.28 (d, 2 H, J = 8.7 Hz), 5.09 (brs, 1 H, OH), 5.08 (d, 1 H, J = 3.6 Hz), 4.89 (d, 1 H, J = 7.2 Hz), 4.61 (brs, 1 H), 3.72 (brd, 1 H, J =11.1Hz),3.48(m,1H). 13 CNMR (75 MHz, DMSO-d 6 ): , , , , , , , , , , , , , , 77.48, 75.87, 73.42, 69.89, ESI-MS (m/z): [M + H + ], [M + ] , 8-Dihydroxyisoflavone 7-O- -L-rhamnopyranoside (26) Compound 26 was obtained as a white foam: [ ] 14 D =-72.4(c 0.61, MeOH); 1 HNMR (300 MHz, DMSO-d 6 ): 9.72 (brs, 1 H), 9.54 (brs, 1 H), 8.40 (s, 1 H), 7.55 (d, 2 H, J = 9.0 Hz), 7.40 (d, 1 H, J = 8.7 Hz), 7.26 (d, 1 H, J = 9.3 Hz), 6.81 (d, 2 H, J =8.1Hz), 5.47 (brs,1 H, OH), 5.06 (brs, 1 H), 4.90 (d, 1 H, J = 5.1 Hz), 4.67 (d, 1 H, J =5.4Hz), 3.98 (brs, 1 H), 3.87 (m, 1 H), 3.55 (m, 1 H), 1.11 (d, 3 H, J =6.3Hz). 13 CNMR(75 MHz, DMSO-d 6 ): , , , , , , , , , , , , , 99.74, 72.03, 70.25, 70.10, 69.98, ESI- MS (m/z): [M + H + ]. HRMS: Calcd for C 21 H 20 O 9 : [M + Na + ]. Found:

14 7.6 Daidzein 7-O- -D-arabinofuranoside (27) Compound 27 was obtained as a white solid: [ ] 14 D = (c 0.22, MeOH); 1 HNMR (300 MHz, 1:1 CD 3 OD-CDCl 3 ): 8.16 (d, 1 H, J = 9.3 Hz), 8.08 (s, 1 H), 7.39 (d, 2 H, J = 8.7 Hz), 7.22 (d, 1 H, J = 2.4 Hz), 7.17 (dd, 1 H, J = 8.7, 2.4 Hz), 6.90 (d, 2 H, J = 8.1 Hz), 5.72 (brs, 1 H), 4.36 (brs, 1 H), 4.17 (m, 1 H), 4.11 (m, 1 H), 3.85 (dd, 1 H, J = 3.0, 12.0 Hz), 3.74 (dd, 1 H, J = 4.2, 12.0 Hz). 13 CNMR(75MHz,1:1CD 3 OD- CDCl 3 ): , , , , , , , , , , , , , 86.92, 82.89, 77.88, ESI-MS (m/z): [M + Na + ], [M + H + ]. HRMS: Calcd for C 20 H 18 O 8 : [M + Na + ]. Found:

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl

More information

Coupling of 6 with 8a to give 4,6-Di-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-Dglucopyranosyl-(1 3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose.

Coupling of 6 with 8a to give 4,6-Di-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-Dglucopyranosyl-(1 3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. General Experimental Procedures. NMR experiments were conducted on a Varian Unity/Inova 400-MHz Fourier Transform NMR Spectrometer. Chemical shifts are downfield from tetramethylsilane in CDCl 3 unless

More information

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde

More information

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Supporting Information

Supporting Information 1 A regiodivergent synthesis of ring A C-prenyl flavones Alberto Minassi, Anna Giana, Abdellah Ech-Chahad and Giovanni Appendino* Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche

More information

Recyclable Enamine Catalysts for Asymmetric Direct Cross-Aldol

Recyclable Enamine Catalysts for Asymmetric Direct Cross-Aldol Recyclable Enamine Catalysts for Asymmetric Direct Cross-Aldol Reaction of Aldehydes in Emulsion Media Qiang Gao, a,b Yan Liu, a Sheng-Mei Lu, a Jun Li a and Can Li* a a State Key Laboratory of Catalysis,

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS OF A 3-THIOMANNOSIDE Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,

More information

Supporting Information

Supporting Information Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry

More information

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi*

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi* Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Solvent-controlled Nucleophilic Trifloromethylthiolation of Morita- Baylis-Hillman

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,

More information

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol.

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol. SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

More information

Supporting Information

Supporting Information Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy

More information

Supporting Information

Supporting Information Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and

More information

Facile Multistep Synthesis of Isotruxene and Isotruxenone

Facile Multistep Synthesis of Isotruxene and Isotruxenone Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:

More information

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Ying Xie, a Hongjie Pan, a Xiao Xiao, a Songlei Li a and Yian Shi* a,b a Beijing National Laboratory for

More information

Supporting Information

Supporting Information Supporting Information Catalytic Site-selective Acylation of Carbohydrates Directed by Cation-n Interaction Guozhi Xiao, 1 Gabriel A. Cintron-Rosado, 2 Daniel A. Glazier, 1,3 Bao-min Xi, 1, Can Liu, 1

More information

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes Supporting Information Curtius-Like Rearrangement of Iron-itrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes Dashan Li,, Ting Wu,, Kangjiang Liang,, and Chengfeng Xia*,, State

More information

hydroxyanthraquinones related to proisocrinins

hydroxyanthraquinones related to proisocrinins Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,

More information

Supporting information

Supporting information Supporting information The L-rhamnose Antigen: a Promising Alternative to α-gal for Cancer Immunotherapies Wenlan Chen,, Li Gu,#, Wenpeng Zhang, Edwin Motari, Li Cai, Thomas J. Styslinger, and Peng George

More information

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of

More information

Supporting Information

Supporting Information Supporting Information A Combined Effect of the Picoloyl Protecting Group and Triflic Acid in Sialylation Samira Escopy, Scott A. Geringer and Cristina De Meo * Department of Chemistry Southern Illinois

More information

Supplementary Information. Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated Glycals and Sulfamate Ester

Supplementary Information. Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated Glycals and Sulfamate Ester Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supplementary Information Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated

More information

Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane

Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane Electronic Supplementary Information (ESI) Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane Jie Liu, ab Qing Meng, a Xiaotao Zhang, a Xiuqiang Lu, a Ping

More information

Supporting Information

Supporting Information Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook

More information

Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012

Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012 Ring Expansion of Alkynyl Cyclopropanes to Highly substituted Cyclobutenes via a N-Sulfonyl-1,2,3-Triazole Intermediate Renhe Liu, Min Zhang, Gabrielle Winston-Mcerson, and Weiping Tang* School of armacy,

More information

Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary

Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources Changqing Rao, Shaoyu Mai and Qiuling Song* Institute of Next

More information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien

More information

Supporting Information For:

Supporting Information For: Supporting Information For: Peptidic α-ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases Yen Ting Chen, Jian Xie, and Christopher T. Seto* Department of Chemistry, Brown

More information

Supporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin*

Supporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin* Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2015 Supporting Information Fluorescent and Colorimetric Probe Containing Oxime-Ether for Pd 2+ in Pure

More information

Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene Supporting Information for Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene Javier Ajenjo 1, Martin Greenhall 2, Camillo Zarantonello 2 and Petr Beier

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro

More information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated

More information

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,

More information

Supporting Information:

Supporting Information: Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:

More information

How to build and race a fast nanocar Synthesis Information

How to build and race a fast nanocar Synthesis Information How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 SUPPORTING INFORMATION Activation of 1, 3-dioxolane by protic ionic liquid in aqueous media:

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi

More information

Supporting Information

Supporting Information Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles** Kohei Fuchibe, Masaki Takahashi,

More information

The all-photochemical Synthesis an. OGP (10-14) Precursor

The all-photochemical Synthesis an. OGP (10-14) Precursor SUPPORTING INFORMATION The all-photochemical Synthesis an OGP (10-14) Precursor Jean-Luc Débieux, Christian G. Bochet* Department of Chemistry, University of Fribourg, 9 Chemin du Musée, CH-1700 Fribourg,

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature16966 Supplementary Synthetic Protocols General Solvents and chemicals were of analytical grade and were purchased from Sigma- Aldrich. Inorganic pyrophosphatase from baker's yeast and

More information

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal

More information

A selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide

A selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information (ESI) A selenium-contained aggregation-induced

More information

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12 Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry

More information

Supporting Information

Supporting Information Supporting Information Lewis acid-catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates Vincent Tran and Thomas G. Minehan * Department of Chemistry and

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Effect of polymer chain conformation on field-effect transistor performance: synthesis and properties of two arylene imide based D-A copolymers Dugang Chen, a Yan Zhao,

More information

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,

More information

Supporting Information:

Supporting Information: Supporting Information: An rganocatalytic Asymmetric Sequential Allylic Alkylation/Cyclization of Morita-Baylis-Hillman Carbonates and 3-Hydroxyoxindoles Qi-Lin Wang a,b, Lin Peng a, Fei-Ying Wang a, Ming-Liang

More information

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one Haoyue Xiang and Chunhao Yang* State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy

More information

PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions

PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions S1 Supporting Information PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions Yanan Zhao, a Jian Li, a Chunju Li, a Kun Yin, a Dongyan Ye a and Xueshun Jia*, a, b a Department

More information

Supporting Information

Supporting Information Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some

More information

Supplementary Information

Supplementary Information Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)

More information

Supporting Information. for. Angew. Chem. Int. Ed Wiley-VCH 2004

Supporting Information. for. Angew. Chem. Int. Ed Wiley-VCH 2004 Supporting Information for Angew. Chem. Int. Ed. 200460176 Wiley-VCH 2004 69451 Weinheim, Germany Iterative ne-pot ligosaccharide Synthesis Xuefei Huang, a * Lijun Huang a, Haishen Wang b, and Xin-Shan

More information

Enhanced Radical-Scavenging Activity of Naturally-Oriented Artepillin C Derivatives

Enhanced Radical-Scavenging Activity of Naturally-Oriented Artepillin C Derivatives Supporting nformation Enhanced Radical-Scavenging Activity of Naturally-Oriented Artepillin C Derivatives Sushma Manda, a kuo Nakanishi,* a,b Kei Ohkubo, b Yoshihiro Uto, c Tomonori Kawashima, b Hitoshi

More information

Synthesis of Bradyrhizose, a Unique Inositol-fused Monosaccharide Relevant to a Nod-factor Independent Nitrogen Fixation

Synthesis of Bradyrhizose, a Unique Inositol-fused Monosaccharide Relevant to a Nod-factor Independent Nitrogen Fixation Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Synthesis of Bradyrhizose, a Unique Inositol-fused Monosaccharide Relevant to a Nod-factor Independent

More information

Kinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker

Kinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker Experimental Materials and Methods. All 31 P NMR and 1 H NMR spectra were recorded on 250 MHz Bruker or DRX 500 MHz instruments. All 31 P NMR spectra were acquired using broadband gated decoupling. 31

More information

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher

More information

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments

More information

Triazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3

Triazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3 Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,

More information

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium Electronic supplementary information For A Heptamethine cyanine -Based Colorimetric and Ratiometric Fluorescent Chemosensor for Selective Detection of Ag + in an Aqueous Medium Hong Zheng *, Min Yan, Xiao-Xing

More information

Supplementary Information. Table of Contents

Supplementary Information. Table of Contents Supplementary Information Modular Chiral Dendritic monodentate phosphoramidite ligands for Rh(I)-Catalyzed Asymmetric Hydrogenation: Unprecedented Enhancement of Enantioselectivity Feng Zhang, a, b Yong

More information

Supplementary Figure 1. 1 H and 13 C NMR spectra for compound S2.

Supplementary Figure 1. 1 H and 13 C NMR spectra for compound S2. Supplementary Figure 1. 1 H and 13 C NMR spectra for compound S2. 1 Supplementary Figure 2. 1 H and 13 C NMR spectra for compound S3. 2 Supplementary Figure 3. 1 H and 13 C NMR spectra for compound S4.

More information

Electronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective

Electronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis** Myles B. Herbert, Vanessa M. Marx, Richard L. Pederson, and Robert

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Concise Stereoselective Synthesis of ( )-Podophyllotoxin by Intermolecular Fe III -catalyzed Friedel-Crafts Alkylation Daniel Stadler, Thorsten

More information

SUPPORTING INFORMATION

SUPPORTING INFORMATION SUPPORTING INFORMATION For Synthesis of Fluorenone Derivatives through Palladium-Catalyzed Dehydrogenative Cyclization Hu Li, Ru-Yi Zhu, Wen-Juan Shi, Ke-Han He, and Zhang-Jie Shi* Beijing National Laboratory

More information

Supporting Information

Supporting Information Meyer, Ferreira, and Stoltz: Diazoacetoacetic acid Supporting Information S1 2-Diazoacetoacetic Acid, an Efficient and Convenient Reagent for the Synthesis of Substituted -Diazo- -ketoesters Michael E.

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002 Supporting Information for Angew. Chem. Int. Ed. Z50016 Wiley-VCH 2002 69451 Weinheim, Germany Total Synthesis of (±)-Wortmannin Takashi Mizutani, Shinobu Honzawa, Shin-ya Tosaki, and Masakatsu Shibasaki*

More information

Supplementary Information (Manuscript C005066K)

Supplementary Information (Manuscript C005066K) Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)

More information

Compound Number. Synthetic Procedure

Compound Number. Synthetic Procedure Compound Number 1 2 3 4 5 Synthetic Procedure Compound 1, KY1220, (Z)-5-((1-(4-nitrophenyl)-1H-pyrrol-2-yl)methylene)-2-thioxoimidazolidin-4-one was purchased from Chemdiv, Catalog #3229-2677, 97% HPLC

More information

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Alan L. Sewell a, Mathew V. J. Villa a, Mhairi Matheson a, William G. Whittingham b, Rodolfo Marquez a*. a) WestCHEM, School of Chemistry,

More information

Supporting Information for. A New Method for the Cleavage of Nitrobenzyl Amides and Ethers

Supporting Information for. A New Method for the Cleavage of Nitrobenzyl Amides and Ethers SI- 1 Supporting Information for A ew Method for the Cleavage of itrobenzyl Amides and Ethers Seo-Jung Han, Gabriel Fernando de Melo, and Brian M. Stoltz* The Warren and Katharine Schlinger Laboratory

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols

Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols

More information

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università

More information

Supporting Information. For. Organic Semiconducting Materials from Sulfur-Hetero. Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical

Supporting Information. For. Organic Semiconducting Materials from Sulfur-Hetero. Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical upporting Information For Organic emiconducting Materials from ulfur-hetero Benzo[k]fluoranthene Derivatives: ynthesis, Photophysical Properties and Thin Film Transistor Fabrication Qifan Yan, Yan Zhou,

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for

More information

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,

More information

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Seyoung Choi and Sangho Koo* Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. E-mail:

More information

Branching of poly(adp-ribose): Synthesis of the Core Motif

Branching of poly(adp-ribose): Synthesis of the Core Motif Branching of poly(adp-ribose): Synthesis of the Core Motif Hans A. V. Kistemaker, Herman S. Overkleeft, Gijsbert A. van der Marel,* and Dmitri V. Filippov* Supporting information Table of contents Experimental

More information

Supplementary Table 1. Small molecule screening data

Supplementary Table 1. Small molecule screening data Supplementary Table 1. Small molecule screening data Category Parameter Description Assay Type of assay Cell-based Target Primary measurement Key reagents Assay protocol PS1/BACE1 interaction Detection

More information

Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones

Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Aurora Martínez-Muñoz, David Monge,* Eloísa Martín-Zamora, Eugenia Marqués-López, Eleuterio Álvarez, Rosario Fernández,*

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,

More information

Supporting Information

Supporting Information Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry

More information

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South

More information

Supramolecular complexes of bambusuril with dialkyl phosphates

Supramolecular complexes of bambusuril with dialkyl phosphates Supramolecular complexes of bambusuril with dialkyl phosphates Tomas Fiala and Vladimir Sindelar RECETX, Masaryk University, Kamenice 5, 62500 Brno, Czech Republic Contents Synthesis... S2 Tripropargyl

More information

Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via

Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions. Guijun Wang,*Jean Rene Ella-Menye, Michael St. Martin, Hao Yang, Kristopher

More information