Branching of poly(adp-ribose): Synthesis of the Core Motif
|
|
- Annabelle Eaton
- 5 years ago
- Views:
Transcription
1 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 procedures NMR Spectra S1- S5 S6- S29
2 General procedures All solvents used under anhydrous conditions were stored over 4Å molecular sieves except for methanol which was stored over 3Å molecular sieves. Solvents used for workup and column chromatography were of technical grade from Sigma Aldrich and used directly. Unless stated otherwise, solvents were removed by rotary evaporation under reduced pressure at 40 C. Reactions were monitored by TLC analysis using Merck 25 DC plastikfolien 60 F254 with detection by spraying with 20% H 2 SO 4 in EtOH, (NH 4 ) 6 Mo 7 O 24 4H 2 O (25 g/l) and (NH 4 ) 4 Ce(SO 4 ) 4 2H 2 O (10 g/l) in 10% sulfuric acid or by spraying with a solution of ninhydrin (3 g/l) in EtOH / AcOH (20/1 v/v), followed by charring at approx. 150 C. Column chromatography was performed by automation using a Biotage Isolera Spektra Four machine. For LC- MS analysis a JASCO HPLC system (detection simultaneously at 214 and 254 nm) equipped with an analytical C18 column (4.6 mmd 50 mml, 3μ particle size) in combination with buffers A: H 2 O, B: MeCN and C: 0.5% aq. TFA and coupled to a PE/SCIEX API 165 single quadruple mass spectrometer (Perkin-Elmer) was used, unless stated otherwise. Alternatively a Thermo Finnigan LCQ Advantage MAX ion-trap mass spectrometer with an electrospray ion source coupled to Surveyor HPLC system (Thermo Finnegan) was used with the same analytical column. High resolution mass spectra were recorded by direct injection (2 μl of a 2 μm solution in water/acetonitrile; 50/50; v/v and 0.1% formic acid) on a mass spectrometer (Thermo Finnigan LTQ Orbitrap) equipped with an electrospray ion source in positive mode (source voltage 3.5 kv, sheath gas flow 10, capillary temperature 250 C) with resolution R = at m/z 400 (mass range m/z = ) and dioctylpthalate (m/z = ) as a lock mass. The high resolution mass spectrometer was calibrated prior to measurements with a calibration mixture (Thermo Finnigan). 1 H and 13 C-NMR spectra were measured on a Brüker AV 400 (400 MHz), Brüker AV 500 (500 MHz) or a AVIII-Brüker DMX 600 (600 MHz) and all individual signal were assigned using 2D-NMR spectroscopy. Chemical shifts are given in ppm (δ) and directly referenced to TMS (0.00 ppm) in CDCl 3 or indirectly referenced to H 3 PO 4 (0.00 ppm) in D 2 O via the solvent residual signal and coupling constants are given in Hz. Infrared (IR) spectra were recorded on a Shimadzu FT-IR ,3,5-tri-O-benzoyl-2-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-α-Dribofuranosyl (4) (N-Phenyl)-2,2,2-trifluoroacetimido-2,3,5-tri-O-benzyl-β-D-ribofuranose [1] (5.7 g, 9.6 mmol) and α-d-ribofuranose 1,3,5-tribenzoate (4.2 g, 9.0 mmol) were coevaporated with 1,4-dioxane (2x) and DCE (1x), dissolved in dry DCM (90 ml) and stirred with freshly activated 3 Å molecular sieves at room temperature for 1 hour under argon to remove traces of water. The solution was then cooled to -78 o C and TMSOTf (17 μl, 1 mol%) was added to the reaction mixture. The reaction was being stirred at the same temperature for 10 minutes after which it was quenched by the addition of triethylamine. The reaction mixture was concentrated in vacuo and purified by silica gel chromatography (Pentane/EA, 90/10 80/20) to afford the title compound as a white foam (6.56 g, 7.59 mmol, 84%). 1 H NMR (500 MHz, CDCl 3 ) δ (m, 4H, arom. Bz), (m, 2H, arom. Bz), (m, 5H, arom.), (m, 5H, arom.), (m, 6H, arom.), (m, 8H, arom.), 6.80 S1
3 (d, J = 4.2 Hz, 1H, H1 ), 5.67 (dd, J = 6.4, 1.9 Hz, 1H, H3 ), 5.29 (d, J = 3.5 Hz, 1H, H1 ), 4.75 (q, J = 3.8 Hz, 1H, H4 ), 4.71 (dd, J = 6.5, 4.3 Hz, 1H, H2 ), 4.66 (AB, J = 12.0, 3.4 Hz, 1H, H5 ), (m, 1H, H5 ), (m, 6H, CH 2 Bn), 4.22 (q, J = 3.6 Hz, 1H, H4 ), (m, 2H, H2, H3 ), 3.46 (AB, J = 10.8, 3.4 Hz, 1H, H5 ), 3.37 (AB, J = 10.8, 3.7 Hz, 1H, H5 ). 13 C NMR (126 MHz, CDCl 3 ) δ , , (CO Bz), , , (cq. arom.), , , (arom.), , (cq. arom.), (arom.), (cq. arom.), , , , , , , , , , , (arom.), (C1 ), (C1 ), (C4 ), (C4 ), (C2 ), (C3 ), (C2 ), 73.48, (CH 2 Bn), (C3 ), (CH 2 Bn), (C5 ), (C5 ). HRMS [C 52 H 48 O 12 + Na] + : found, calculated 1,3,5-tri-O-benzoyl-2-O-(3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3- diyl)-α-d-ribofuranosyl)-α-d-ribofuranosyl (5) Compound 4 (1.32 g, 7.3 mmol) was dissolved in tbuoh/dioxane/h 2 O (90 ml, 4/4/1; v/v/v) and Pd/C (600 mg, 10 wt. % Pd) was added. H 2 (g) was bubbled through the solution for 16 hours after which the reaction mixture was filtered over celite, concentrated in vacuo and co-evaporated with toluene (2x). Imidazole (1.49 g, 22 mmol) was added to the crude reaction mixture and coevaporated with toluene (2x). The mixture was dissolved in DCM (70 ml) and 1,3-dichloro-1,1,3,3- tetraisopropyldisiloxane (2.8 ml, 8.8 mmol) was added. The reaction was stirred at room temperature for 30 minutes and quenched upon the addition of H 2 O. The organic layer was washed with brine, dried over MgSO 4, concentrated under reduced pressure and purified by silica gel chromatography (eluting with Pentane/EA, 95/5 90/10) to obtain the product as a white foam (1.75 g, 2.09 mmol, 29%). 1 H NMR (500 MHz, CDCl 3 ) δ 8.15 (dd, J = 8.3, 1.2 Hz, 2H, Bz), 8.11 (dd, J = 8.3, 1.2 Hz, 2H, Bz), 8.07 (dd, J = 8.3, 1.2 Hz, 2H, Bz), (m, 3H, Bz), (m, 2H, Bz), (m, 4H, Bz), 6.79 (d, J = 4.2 Hz, 1H, H1 ), 5.67 (dd, J = 6.3, 2.1 Hz, 1H, H3 ), 5.18 (d, J = 4.2 Hz, 1H, H1 ), 4.77 (q, J = 3.6 Hz, 1H, H4 ), 4.75 (dd, J = 6.3, 4.2 Hz, 1H, H2 ), 4.67 (AB, J = 12.1, 3.3 Hz, 1H, H5 ), 4.62 (AB, J = 12.1, 3.9 Hz, 1H, H5 ), (m, 1H, H3 ), (m, 1H, H2 ), 3.92 (ddd, J = 8.4, 4.9, 3.6 Hz, 1H, H4 ), 3.81 (AB, J = 11.7, 3.6 Hz, 1H, H5 ), 3.65 (AB, J = 11.7, 8.3 Hz, 1H, H5 ), 2.85 (d, J = 8.6 Hz, 1H, OH), 1.03 (t, J = 6.5 Hz, 12H, CH 3 TIPDS), 0.97 (d, J = 3.0 Hz, 6H, CH 3 TIPDS), 0.96 (d, J = 2.1 Hz, 6H, CH 3 TIPDS), 0.80 (d, J = 7.3 Hz, 2H, CH TIPDS), 0.73 (d, J = 7.3 Hz, 2H, CH TIPDS). 13 C NMR (126 MHz, CDCl 3 ) δ , (CO Bz), , , , , , (arom.), (cq. arom.), , , (arom.), (C1 ), (C1 ), (C4 ), (C4 ), (C2 ), (C3 ), (C2 ), (C3 ), (C5 ), (C5 ), 17.57, 17.51, 17.47, 17.43, 17.22, 17.19, 17.09, 16.85, 16.71, 13.48, 13.29, 13.19, 13.06, (CH, CH 3, TIPDS). HRMS [C 43 H 56 O 13 Si 2 + Na] + : found, calculated 1,3,5-tri-O-benzoyl-2 -O-(2 -O-(2,3-di-O-benzyl-5-Otriisopropylsilyl-α-D-ribofuranosyl)- 3,5-O-(1,1,3,3- tetraisopropyldisiloxane-1,3-diyl)- α-d-ribofuranosyl)-α-dribofuranosyl (6) (N-Phenyl)-2,2,2-trifluoroacetimido-5-triisopropylsilyl-2,3-O-benzyl-α,β- D-ribofuranose [2] (1.97 g, 3.0 mmol) and compound 5 (1.67 g, 2.0 mmol) were co-evaporated with 1,4-dioxane (2x), dissolved in dry DCM (40 ml) and left to stand with freshly activated 3 Å molecular sieves at room temperature for 16 hour under argon to remove traces of water. The solution was then cooled to -78 o C and TMSOTf (12 μl, 2 mol%) was added to the reaction mixture. The reaction was being stirred at the same temperature for 30 minutes after which it was quenched by the addition of triethylamine. The S2
4 reaction mixture was concentrated in vacuo and purified by silica gel chromatography (Pentane/EA, 95/5 90/10 85/15 ) to afford the title compound as a white foam (1.47 g, 1.13 mmol, 57%). 1 H NMR (500 MHz, CDCl 3 ) δ (m, 2H, Bz), (m, 4H, Bz), (m, 2H, Bz), (m, 3H, Bz), (m, 2H, arom.), (m, 7H, arom.), (m, 5H, arom.), 6.78 (d, J = 4.1 Hz, 1H, H1 ), 5.59 (dd, J = 6.2, 1.8 Hz, 1H, H3 ), 5.35 (d, J = 3.5 Hz, 1H, H1 ), 5.27 (d, J = 3.9 Hz, 1H, H1 ), 4.83 (dd, J = 6.2, 4.2 Hz, 1H, H2 ), 4.71 (d, J = 11.4 Hz, 1H, CH 2 Bn), (m, 1H, H4 ), 4.62 (AB, J = 12.0, 3.4 Hz, 1H, H5 ), 4.51 (AB, J = 12.0, 4.1 Hz, 1H, H5 ), 4.43 (d, J = 11.9 Hz, 1H, CH 2 Bn), 4.40 (dd, J = 5.1, 3.6 Hz, 1H, H2 ), 4.31 (d, J = 11.8 Hz, 1H, CH 2 Bn), (m, 2H, H3, H4 ), 4.04 (dt, J = 8.8, 2.2 Hz, 1H, H4 ), 3.96 (d, J = 11.4 Hz, 1H, CH 2 Bn), 3.81 (AB, J = 13.0, 2.0 Hz, 1H, H5 ), (m, 2H, H3, H5 ), 3.71 (AB, J = 10.9, 3.2 Hz, 1H, H5 ), 3.66 (AB, J = 11.0, 3.2 Hz, 1H, H5 ), 3.43 (dd, J = 6.4, 3.9 Hz, 1H, H2 ), (m, 45H, CH, CH 3, TIPDS, TIPS), (m, 4H, CH, TIPDS). 13 C NMR (126 MHz, CDCl 3 ) δ , , (CO Bz), , (cq. arom.), , , , (arom.), (cq. arom.), , (arom.), , (cq. arom.), , , , , , , , , (arom.), (C1 ), (C1 ), (C1 ), (C4 ), 81.24, (C4, C4 ), (C2 ), (C3 ), (C2 ), (C2 ), (C3 ), 72.35, (CH 2 Bn), (C3 ), (C5 ), (C5 ), (C5 ), 18.11, 17.55, 17.50, 17.44, 17.25, 17.21, 17.12, 16.99, 13.65, 13.18, 12.82, 12.64, (CH, CH 3, TIPS, TIPDS). HRMS [C 71 H 96 O 17 Si 3 + Na] + : found, calculated 1,3,5-tri-O-benzoyl-2 -O-(2 -O-(2,3-di-O-acetyl-5-Otriisopropylsilyl-α-D-ribofuranosyl)- 3-O-acety l-5-otertbutyldiphenylsilyl- α-d-ribofuranosyl)-α-d-ribofuranosyl (7) Compound 6 (1.43 g, 1.1 mmol) was dissolved in tbuoh/dioxane/h 2 O (20 ml, 4/4/1; v/v/v) and Pd/C (110 mg, 10 wt. % Pd) was added. H 2 (g) was bubbled through the solution for 16 hours. TLC and TLC-MS analysis indicated no complete conversion and additional Pd/C (250 mg) was added. The reaction was stirred for 2 days after which the reaction mixture was filtered over celite, concentrated in vacuo and co-evaporated with pyridine (2x). The mixture was dissolved in pyridine (10 ml) and HF.pyridine (1.3 ml) was added. The reaction was stirred at room temperature for 1.5 hour and quenched by the carefull addition of aq. NaHCO 3 (sat.). The mixture was extracted with DCM (2x), the organic layers were dried (MgSO 4 ) and concentrated under reduced pressure. The crude was coevaporated with pyridine (2x) and dissolved in pyridine (15 ml). Tert-butyldiphenylsilyl chloride (0.57 ml, 2.2 mmol) was added and the mixture was stirred at room temperature for 16 hours. Acetic anhydride (3 ml, 30 mmol) was added and the reaction was stirred for 6 hours. The reaction mixture was concentrated, dissolved in EtOAc and washed with aq. HCl (1M). The organic layer was washed with aq. NaHCO 3 (sat.), dried (MgSO 4 ) and concentrated in vacuo. Purification by silica gel chromatography (Pentane/EA, 90/10 85/15 80/20 ) afforded the title compound as a white foam (444 mg, 0.36 mmol, 33%). 1 H NMR (500 MHz, CDCl 3 ) δ 8.20 (d, J = 7.3 Hz, 2H, Bz), 8.16 (d, J = 7.3 Hz, 2H, Bz), 8.07 (d, J = 7.4 Hz, 2H, Bz), (m, 7H, arom.), (m, 12H, arom.), 6.78 (d, J = 4.3 Hz, 1H, H1 ), 5.71 (dd, J = 6.3, 1.5 Hz, 1H, H3 ), 5.47 (dd, J = 6.5, 1.6 Hz, 1H, H3 ), (m, 3H, H1, H1, H3 ), 4.81 (dd, J = 6.9, 4.5 Hz, 1H, H2 ), (m, 1H, H4 ), 4.67 (AB, J = 12.0, 3.4 Hz, 1H, H5 ), 4.62 (AB, J = 12.1, 4.2 Hz, 1H, H5 ), 4.59 (dd, J = 6.2, 4.5 Hz, 1H, H2 ), 4.35 (dd, J = 6.5, 4.3 Hz, 1H, H2 ), (m, 2H, H4, H4 ), 3.88 (AB, J = 10.9, 2.5 Hz, 1H, H5 ), 3.75 (AB, J = 10.9, 2.8 Hz, 1H, H5 ), 3.65 (AB, J = 11.2, 2.6 Hz, 1H, H5 ), 3.61 (AB, J = 11.3, 3.1 Hz, 1H, H5 ), 2.01 (s, 3H, CH 3 Ac), 1.78 (s, 3H, CH 3 Ac), 1.66 (s, 3H, CH 3 Ac), (m, 21H, CH, CH 3, TIPS), 1.00 (s, 9H, CH 3 TBDPS). S3
5 13 C NMR (126 MHz, CDCl 3 ) δ , , (CO Ac), , , (CO Bz), , , , (arom.), , , (cq. arom.), , (arom.), (cq. arom.), , , (arom.), (cq. arom.), , , , (arom.), (C1 ), (C1 ), (C1 ), 83.83, 83.64, (C4, C4, C4 ), (C2 ), (C2 ), (C3 ), (C2 ), (C3 ), (C3 ), (C5 ), (C5 ), (C5 ), (CH 3 TBDPS), 20.71, 20.43, (CH 3 Ac), (cq. TBDPS), 18.07, 18.06, (CH, CH 3, TIPS). HRMS [C 67 H 82 O 19 Si 2 + Na] + : found, calculated N 6 -benzoyl-9-[3,5-di-o-benzoyl-2-o-(2 -O-(2,3-di-O-acetyl-5-Otriisopropylsilyl-α-D-ribofuranosyl)-3-O-acetyl-5-Otertbutyldiphenylsilyl-α-D-ribofuranosyl)- -D-ribofuranosyl]- adenine (8) Compound 7 (311 mg, 0.25 mmol) and N 6 -benzoyladenine (120 mg, 0.5 mmol) were co-evaporated with dioxane (3x) and MeCN (1x) and dissolved in MeCN (4 ml) under an argon atmosphere. N,Obis(trimethylsilyl)trifluoroacetamide (BSTFA) (0.4 ml, 1.5 mmol) was added and the mixture was stirred at room temperature until everything was dissolved. HClO 4 -SiO 2 (312 mg, 0.5 eq; 0.4 mmol/g) was added and the mixture was refluxed for 2 hours. TLC analysis showed no complete conversion and additional HClO 4 -SiO 2 (312 mg, 0.5 eq) was added. The mixture was refluxed for two more hours, filtered and concentrated in vacuo. Purification by silica gel chromatography (eluting with DCM/EA, 100/0 90/10 80/20 70/30) yielded the product as a white foam (215 mg, 0.16mmol, 63%). 1 H NMR (600 MHz, CDCl 3 ) δ 9.12 (s, 1H, NH), 8.67 (s, 1H, H2), 8.39 (s, 1H, H8), 8.07 (t, J = 8.2 Hz, 4H, arom.), 8.03 (d, J = 7.5 Hz, 2H, arom.), (m, 9H, arom.), (m, 10H, arom.), 6.31 (d, J = 4.6 Hz, 1H, H1 ), 5.93 (t, J = 5.4 Hz, 1H, H3 ), 5.66 (t, J = 5.0 Hz, 1H, H2 ), 5.45 (dd, J = 6.9, 2.2 Hz, 1H, H, H3 ), 5.30 (dd, J = 7.2, 3.2 Hz, 1H, H3 ), 5.24 (d, J = 4.4 Hz, 1H, H1 ), 5.13 (d, J = 4.4 Hz, 1H, H1 ), 4.88 (AB, J = 12.1, 3.7 Hz, 1H, H5 ), 4.84 (dd, J = 7.2, 4.4 Hz, 1H, H2 ), (m, 1H, H4 ), 4.69 (AB, J = 12.1, 4.9 Hz, 1H, H5 ), 4.31 (dd, J = 6.8, 4.4 Hz, 1H, H2 ), 4.08 (q, J = 2.8 Hz, 1H, H4 ), 3.99 (q, J = 2.5 Hz, 1H, H4 ), 3.86 (AB, J = 11.1, 2.5 Hz, 1H, H5 ), 3.75 (AB, J = 11.1, 3.0 Hz, 1H, H5 ), 3.57 (AB, J = 11.2, 2.6 Hz, 1H, H5 ), 3.43 (AB, J = 11.3, 3.2 Hz, 1H, H5 ), 2.11 (s, 3H, CH 3 Ac), 2.06 (s, 3H, CH 3 Ac), 1.69 (s, 3H, CH 3 Ac), (m, 30H, CH, CH 3, TIPS, TBDPS). 13 C NMR (151 MHz, CDCl 3 ) δ , , (CO Ac), , , (CO Bz), (CH C2), (C4), (C6), (CH C8), , (arom.), (cq. arom.), , (arom.), (cq. arom.), (arom.), (cq. arom.), , , (arom.), , (cq. arom.), , , , , , (arom.), (C5), (C1 ), (C1 ), (C1 ), (C4 ), (C4 ), (C4 ), (C2 ), (C2 ), (C3 ), (C2 ), (C3 ), (C3 ), (C5 ), (C5 ), C5 ), (CH 3 TBDPS), 20.80, 20.68, (CH 3 Ac), (cq. TBDPS), 18.01, 17.99, (CH, CH 3, TIPS). HRMS [C 72 H 85 N 5 O 18 Si 2 + H] + : found, calculated N 6 -benzoyl-9-[3,5-di-o-benzoyl-2-o-(2 -O-(2,3-di-O-acetyl-5- O-triisopropylsilyl-α-D-ribofuranosyl)-3-O-acetyl-α-Dribofuranosyl)- -D-ribofuranosyl]-adenine (9) Compound 8 (30 mg, 22 mol) was dissolved in pyridine (1 ml) and HF.pyridine (50 L) was added. The mixture was stirred at room temperature for 1 hour after which it was quenched by the carefull addition of aq. NaHCO 3 (sat.). The mixture was extracted with DCM (2x) and the organic layers dried over MgSO 4. After concentration under reduced pressure, the crude was purified by silica gel S4
6 chromatography (DCM/EA, 70/30 50/50) to afford the title compound as a white foam (18 mg, 16 mol, 73%). 1 H NMR (500 MHz, CDCl 3 ) δ 8.66 (s, 1H, H2), 8.38 (s, 1H, H8), 8.11 (d, J = 7.7 Hz, 2H, Bz), 8.06 (d, J = 7.5 Hz, 2H, Bz), 8.03 (d, J = 7.7 Hz, 2H, Bz), (m, 2H, Bz), (m, 3H, Bz), (m, 4H, Bz), 6.31 (d, J = 4.4 Hz, 1H, H1 ), (m, 1H, H3 ), 5.71 (t, J = 4.8 Hz, 1H, H2 ), 5.27 (dd, J = 7.1, 3.0 Hz, 1H, H3 ), (m, 1H, H1 ), 5.21 (dd, J = 7.1, 3.0 Hz, 1H, H3 ), 5.12 (d, J = 4.3 Hz, 1H, H1 ), (m, 2H, H2, H5 ), 4.76 (q, J = 4.5 Hz, 1H, H4 ), 4.69 (AB, J = 12.0, 4.7 Hz, 1H, H5 ), 4.15 (dd, J = 6.8, 3.7 Hz, 1H, H2 ), 4.06 (d, J = 2.6 Hz, 1H, H4 ), 4.01 (d, J = 2.7 Hz, 1H, H4 ), 3.83 (AB, J = 10.9, 2.5 Hz, 1H, H5 ), 3.73 (AB, J = 10.9, 2.6 Hz, 1H, H5 ), (m, 2H, H5 ), 2.08 (s, 3H, CH 3 Ac), 2.05 (s, 3H, CH 3 Ac), 1.68 (s, 3H, CH 3 Ac), (m, 21H, CH, CH 3, TIPS). 13 C NMR (126 MHz, CDCl 3 ) δ , , (CO Ac), , (CO Bz), (C4), (C6), (arom.), (cq. arom.), , , , (arom.), (cq. arom.), , , , (arom.), (C5), (C1 ), (C1 ), (C1 ), (C4, C4 ), (C4 ), (C2 ), (C2 ), (C3 ), (C2 ), (C3 ), (C3 ), (C5 ), (C5 ), (C5 ), 29.83, 20.77, 20.70, (CH 3 Ac), 18.02, 18.00, (CH, CH 3, TIPS). HRMS [C 56 H 67 N 5 O 18 Si + H] + : found, calculated 9-[2 -O-((2 -O-(α-D-ribofuranosyl)-α-D-ribofuranosyl)-β-Dribofuranosyl]-adenine (10) Compound 8 (136 mg, 100 mol) was dissolved in THF (2 ml) and tetrabutylammonium fluoride (TBAF) (0.3 ml; 1M in THF) was added. After 2 hours additional TBAF (0.6 ml) was added and the reaction was stirred for 16 hours at room temperature. The reaction mixture was transferred to a microwave vial, aq. NH 4 OH (30%) (10 ml) was added and the vial was sealed with a septum. The mixture was stirred at 50 o C for 16 hours, concentrated in vacuo and purified over HW-40 gel filtration (0.15 M, ammonium acetate). Repeated lyophilization yielded the title compound as a white solid (41 mg, 76 mol, 76%). 1 H NMR (500 MHz, D 2 O) δ 8.35 (s, 1H, H8), 8.16 (s, 1H, H2), 6.20 (d, J = 6.6 Hz, 1H, H1 ), 5.25 (d, J = 3.6 Hz, 1H, H1 ), 4.96 (d, J = 4.0 Hz, 1H, H1 ), 4.90 (dd, J = 6.5, 5.1 Hz, 1H, H2 ), 4.56 (dd, J = 5.1, 2.7 Hz, 1H, H3 ), 4.35 (q, J = 3.0 Hz, 1H, H4 ), (m, 1H, H4 ), (m, 2H, H2, H3 ), (m, 1H, H4 )), (m, 2H, H2, H3 ), 3.96 (AB, J = 12.9, 2.8 Hz, 1H, H5 ), 3.88 (AB, J = 12.9, 3.5 Hz, 1H, H5 ), 3.73 (AB, J = 12.4, 3.4 Hz, 2H, H5, H5 ), 3.65 (dt, J = 12.3, 5.1 Hz, 2H, H5, H5 ). 13 C NMR (126 MHz, D 2 O) δ (C6), (C2), (C4), (C8), (C5), (C1 ), (C1 ), (C1 ), (C4 ), (C4 ), (C4 ), (C2 ), (C2 ), (C2 ), (C3 ), (C3 ), (C3 ), 61.55, 61.37, (C5, C5, C5 ). HRMS [C 20 H 29 N 5 O 12 + Na] + : found, calculated [1] G. J. van der Heden van Noort, H. S. Overkleeft, G. A. van der Marel, D. V. Filippov, Org. Lett. 2011, 13, [2] H. A. V. Kistemaker, G. J. van der Heden van Noort, H. S. Overkleeft, G. A. van der Marel, D. V. Filippov, Org. Lett. 2013, 15, S5
7 Compound 4, 1 H NMR 500 MHz, CDCl 3 S6
8 Compound 4, 13 C NMR 126 MHz, CDCl 3 S7
9 Compound 4, HSQC-HECADE S8
10 Compound 4, HSQC-HECADE S9
11 Compound 5, 1 H NMR 500 MHz, CDCl 3 S10
12 Compound 5, 13 C NMR 126 MHz, CDCl 3 S11
13 Compound 6, 1 H NMR 500 MHz, CDCl 3 S12
14 Compound 6, 13 C NMR 126 MHz, CDCl 3 S13
15 Compound 6, HSQC-HECADE S14
16 Compound 6, HSQC-HECADE S15
17 Compound 7, 1 H NMR 500 MHz, CDCl 3 S16
18 Compound 7, 13 C NMR 126 MHz, CDCl 3 S17
19 Compound 8, 1 H NMR 600 MHz, CDCl 3 S18
20 Compound 8, 13 C NMR 151 MHz, CDCl 3 S19
21 Compound 8, HSQC-HECADE S20
22 Compound 8, HSQC-HECADE S21
23 Compound 9, 1 H NMR 500 MHz, CDCl 3 S22
24 Compound 9, 13 C NMR 126 MHz, CDCl 3 S23
25 Compound 10, 1 H NMR 500 MHz, D 2 O S24
26 Compound 10, 1 H NMR 500 MHz, D 2 O, H 2 O suppression S25
27 Compound 10, 13 C NMR 126 MHz, D 2 O S26
28 Compound 10, 1 H NMR 400 MHz, D 2 O, COSY S27
29 Compound 10, 1 H NMR 400 MHz, D 2 O, HSQC S28
30 Compound 10, 1 H NMR 400 MHz, D 2 O, HMBC S29
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 informationSupporting 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 informationSupporting 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 informationAn 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 informationSYNTHESIS 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 informationSupporting 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 informationSupporting 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 informationKinetics 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 informationThe 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 informationFast 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 informationSupporting Information
Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,
More informationSupporting 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 informationSupporting 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 informationSynthetic 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 informationSupporting 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 informationSupporting 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 informationSupporting 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 informationSupporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra
Supporting Information for Sonogashira Hagihara reactions of halogenated glycals Dennis C. Koester and Daniel B. Werz* Address: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität
More informationAccessory Information
Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department
More informationSupplemental data. Supplemental Figure 1: Alignment of potential ERRE1 and 2 in human, mouse and rat. PEPCK promoter.
1 Supplemental data A Supplemental Figure 1: Alignment of potential ERRE1 and 2 in human, mouse and rat PEPCK promoter. 2 A B C Supplemental Figure 2: Molecular structures of 4-T analogs. a-b, GSK5182
More informationSupporting 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 informationSUPPLEMENTARY 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 informationSupporting 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 informationSupporting Information
Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of
More informationCatalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions
SUPPORTIG IFORMATIO Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions Alexey Volkov, a Fredrik Tinnis, a and Hans Adolfsson.* a a Department of Organic Chemistry,
More informationSUPPLEMENTARY 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 informationSUPPLEMENTARY INFORMATION
doi:10.1038/nature22309 Chemistry All reagents and solvents were commercially available unless otherwise noted. Analytical LC-MS was carried out using a Shimadzu LCMS-2020 with UV detection monitored between
More informationCoupling 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 informationFacile Synthesis of Flavonoid 7-O-Glycosides
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 116023, China
More informationSupporting 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 informationSupporting 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 informationSynthesis of borinic acids and borinate adducts using diisopropylaminoborane
Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,
More informationElectronic Supplementary Material (ESI) for Medicinal Chemistry Communications This journal is The Royal Society of Chemistry 2012
Supporting Information. Experimental Section: Summary scheme H 8 H H H 9 a H C 3 1 C 3 A H H b c C 3 2 3 C 3 H H d e C 3 4 5 C 3 H f g C 2 6 7 C 2 H a C 3 B H c C 3 General experimental details: All solvents
More informationTriazabicyclodecene: 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 informationFormal 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 informationTotal Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig. M. Williams. Supporting Information
Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig M. Williams Supporting Information General Methods S-2 Experimental S-2 1 H and 13 C NMR Spectra S-7 Comparison:
More informationSynthesis 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 informationSelective 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 informationSupporting 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 informationSynthesis 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 informationElectronic Supplementary Information
Electronic Supplementary Information General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water Dong-Hwan Lee, Ji-Young Jung, and Myung-Jong
More informationSupporting Information. Identification and synthesis of impurities formed during sertindole
Supporting Information Identification and synthesis of impurities formed during sertindole preparation I. V. Sunil Kumar* 1, G. S. R. Anjaneyulu 1 and V. Hima Bindu 2 for Address: 1 Research and Development
More informationDual Catalyst System provides the Shortest Pathway for l-menthol Synthesis
Chemical Communications Supporting Information Dual Catalyst System provides the Shortest Pathway for l-menthol Synthesis Hironori Maeda, Shinya Yamada, Hisanori Itoh, and Yoji Hori* Takasago International
More informationSupporting 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 informationEfficient 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 informationA Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
More informationSynthesis 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 informationSupporting information
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 205 A simple and greener approach
More informationAziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize
More informationFlaws in foldamers: screw- sense fidelity and signal decay in achiral helical peptide oligomers
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2015 Flaws in foldamers: screw- sense fidelity and signal decay in achiral helical peptide oligomers
More informationLight-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 informationSupporting 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 informationSupporting Information. Microwave-Assisted Preparation of Nucleoside-Phosphoramidites
Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2014 Supporting Information Microwave-Assisted Preparation of Nucleoside-Phosphoramidites
More informationSUPPORTING INFORMATION
Dynamic covalent templated-synthesis of [c2]daisy chains. Altan Bozdemir, a Gokhan Barin, a Matthew E. Belowich, a Ashish. Basuray, a Florian Beuerle, a and J. Fraser Stoddart* ab a b Department of Chemistry,
More informationSelective Synthesis of 1,2- cis- α- Glycosides in the Absence of Directing Groups. Application to Iterative Oligosaccharide Synthesis.
Selective Synthesis of 1,2- cis- α- Glycosides in the Absence of Directing Groups. Application to Iterative ligosaccharide Synthesis. An- Hsiang Adam Chu, Son Hong Nguyen, Jordan A Sisel, Andrei Minciunescu,
More informationSupporting Information for
Electronic Supplementary Material (ES) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Supporting nformation for BODPY-Containing
More informationSupplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view.
Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view. (b) Side view. All hydrogen atoms are omitted for clarity.
More informationRed 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 informationAn unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters
S1 An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters Chris V. Galliford and Karl A. Scheidt* Department of Chemistry, Northwestern University, 2145 Sheridan
More informationSupporting 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 informationSupporting 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 informationSupplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008
Supplementary Information for: Scrambling Reaction between Polymers Prepared by Step-growth and Chain-growth Polymerizations: Macromolecular Cross-metathesis between 1,4-Polybutadiene and Olefin-containing
More informationSynthesis 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 informationPhotooxidations 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 informationTuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts
More informationSupporting Information
Supporting Information Synthesis of the natural product Marthiapeptide A Yuqi Zhang 1, Md. Amirul Islam 1 and Shelli R. McAlpine 1* 1 School of Chemistry, University of New South Wales, Sydney, NSW 2052
More informationBrønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis
Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School
More informationSupporting information
Supporting information Taking control of P1, P1 and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics Daniel Wiktelius and Kristina Luthman* Department
More informationReduction-free synthesis of stable acetylide cobalamins. Table of Contents. General information. Preparation of compound 1
Electronic Supporting Information Reduction-free synthesis of stable acetylide cobalamins Mikołaj Chromiński, a Agnieszka Lewalska a and Dorota Gryko* a Table of Contents General information Numbering
More informationSupporting 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 informationIndium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols
Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry
More informationAnion recognition in water by a rotaxane containing a secondary rim functionalised cyclodextrin stoppered axle
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary Information: Anion recognition in water by a rotaxane containing a secondary rim
More informationA Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J.
A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones Jin-Quan Yu, a and E. J. Corey b * a Department of Chemistry, Cambridge University, Cambridge CB2 1EW, United
More informationSUPPORTING 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 informationSupplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.
Tetrahedron Letters 1 Pergamon TETRAHEDRN LETTERS Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Jennifer L. Stockdill,
More informationScalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis
Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis Fei Yu, Matthew S. McConnell, and Hien M. Nguyen* Department of Chemistry, University of Iowa, Iowa
More informationSupporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions Patrick S. Fier* and Kevin M. Maloney* S1 General experimental details All reactions
More informationHighly stereocontrolled synthesis of trans-enediynes via
Supporting Information for Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes Tsutomu Konno*, Misato Kishi, and Takashi Ishihara Address: Department of Chemistry
More informationSupporting 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 informationReactions. James C. Anderson,* Rachel H. Munday. School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK
Vinyl-dimethylphenylsilanes as Safety Catch Silanols in Fluoride free Palladium Catalysed Cross Coupling Reactions. James C. Anderson,* Rachel H. Munday School of Chemistry, University of Nottingham, Nottingham,
More informationSUPPORTING INFORMATION. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore
SUPPORTING INFORMATION A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore Serdar Atilgan,, Tugba Ozdemir, and Engin U. Akkaya * Department
More informationHow 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 informationRegioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System
Regioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System Doris Lee and Mark S. Taylor* Department of Chemistry, Lash Miller Laboratories, University of Toronto 80 St.
More informationStraightforward 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 informationChemically Linked Vemurafenib Inhibitors Promote an Inactive BRAF V600E Conformation
Chemically Linked Vemurafenib Inhibitors Promote an Inactive BRAF V600E Conformation Michael Grasso 1,2,*, Michelle A. Estrada 2,*, Christian Ventocilla 2, Minu Samanta 3, Jasna Maskimoska 2, Jessie Villanueva
More informationSupporting 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 informationSupporting Information
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry Supporting Information General Remarks Most of chemicals were purchased from Sigma-Aldrich, Strem,
More informationPhil S. Baran*, Ryan A. Shenvi, Christos Mitsos SUPPORTING INFORMATION
A Remarkable Ring Contraction En Route to the Chartelline Alkaloids Phil S. Baran*, Ryan A. Shenvi, Christos Mitsos Contribution from the Department of Chemistry, The Scripps Research Institute, 10550
More informationSynthesis and structural analysis of anilides of. glucuronic acid and orientation of groups on
Synthesis and structural analysis of anilides of glucuronic acid Tosin, Brien et al. S1 Synthesis and structural analysis of anilides of glucuronic acid and orientation of groups on carbohydrate scaffolding.
More informationSupporting Information File 1. for. Useful Access to Enantiomerically Pure Protected Inositols from Carbohydrates: the Aldohexos-5-uloses Route
Supporting Information File 1 for Useful Access to Enantiomerically Pure Protected Inositols from Carbohydrates: the Aldohexos-5-uloses Route Felicia D Andrea, 1 Giorgio Catelani, 1 Lorenzo Guazzelli,*,1
More informationFacile 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 informationDivergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site
More informationSupporting Information
Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and
More informationSupporting 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 informationBulletin of the Chemical Society of Japan
Supporting Information Bulletin of the Chemical Society of Japan Enantioselective Copper-Catalyzed 1,4-Addition of Dialkylzincs to Enones Followed by Trapping with Allyl Iodide Derivatives Kenjiro Kawamura,
More informationfor Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl Compounds by Iminoiodanes
10.1071/CH16580_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(4), 430-435 Supplementary Material for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl
More informationDomino 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 informationRh(III)-catalyzed Redox-Neutral Unsymmetrical C-H. Alkylation and Amidation Reactions of
Rh(III)-catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides Yunxiang Wu, a,b, Zhaoqiang Chen, c, Yaxi Yang, a,b Weiliang Zhu,*,c Bing Zhou*,a,b a Department
More informationhydroxyanthraquinones 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 informationA 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