VEBSA, RRR-VEPSA, RRR-VEBPA, RRR-VEPPA) was obtained from the hydrolysis of the
|
|
- Rodney Bishop
- 5 years ago
- Views:
Transcription
1 Supplemental Material and thods Synthesis of α-vitamin E analogs All racemic α-tocopherol (synthetic compound) was purchased from Acros (Morris Plains, NJ) and was used to synthesize the all-racemic α-tocopherol analogs (VES, VEBSA, VEPSA). R,R,R-α-Tocopherol, used to synthesize the R,R,R-α-tocopherol analogs (RRR- VEBSA, RRR-VEPSA, RRR-VEBPA, RRR-VEPPA) was obtained from the hydrolysis of the succinate ester of (+)-α-tocopherol succinate, which was purchased from Sigma-Aldrich (St. Louis, M). All-racemic α-tocopherol succinate (rac-ves) was obtained in one step via esterification of α-tocopherol with succinic anhydride in the presence of 4-(dimethylamino)pyridine (DMAP) (eq.1) The sulfonic acid analogs, VEBSA and VEPSA, were synthesized from α-tocopherol by alkylation of the alkoxide of α-tocopherol with 1,3-propane sultone and 1,4-butane sultone, respectively (eq.2). The phosphonic acid analogs, RRR-VEBPA and RRR-VEPPA, were synthesized from R,R,R-α-tocopherol via 5-step sequences involving alkylation with 3- bromopropanol or 4-bromobutanol, respectively, followed by conversion of the terminal alcohol to an iodide. The iodide was displaced with triethylphosphite and the resulting phosphonates were subsequently hydrolyzed to afford the phosphonic acids (eq.3). 1
2 H all racemic α-tocopherol DMAP, CH 2 Cl 2, 23 C H all-racemic VES (1) H 1) NaH, THF, then 3) HCl 2 S n H 2 S n n = 1, R,R,R-VEPSA n = 2, R,R,R-VEBSA (2) H 1) NaH, THF, then BrCH 2 (CH 2 ) n CH 2 H 2) MsCl, Et 3 N 3) NaI 4) (Et 3 )P, Δ 5) HCl, Δ (H) 2 P n n = 1, R,R,R-VEPPA n = 2, R,R,R-VEBPA (3) Experiments for the Synthesis of Vitamin E Analogs General Experimental Information: All reagents used were purchased from Aldrich or Acros. Solvents were purified using a solvent filtration system purchased from Contour Glass Co. (Irvine, California). R,R,R-α-Tocopherol was obtained in gram quantities by saponification (Kt-Bu, H) of commercially available (Sigma Aldrich) (+)-α-tocopherol succinate. 1 H NMR data were obtained in CDCl 3 (using 7.26 ppm for reference of residual CHCl 3 ) at 300, 400, or 500 MHz using Varian instruments. 13 C NMR data in CDCl 3 (using 77.0 ppm as internal reference) were obtained at 75.5 MHz. ptical Rotations were obtained using a JASC DIP-370 digital polarimeter. UV/Vis spectra were obtained in chloroform and ethanol using a Hewlett Packard 8452A Diode Array spectrophotometer. IR spectra were obtained neat from thin films using a Nicolet Avatar 330 FTIR. High resolution mass spectra were obtained at SUNY, Buffalo s Mass Spec. facility on a ThermoFinnigan MAT XL spectrophotometer purchased by a National Science Foundation grant to the center (NSF CHE ). The melting points reported are uncorrected. 2
3 MgS 4, filtered, and concentrated in vacuo. Flash chromatography of the crude oil on Si 2 (10-60% EtAc/hexanes gradient) afforded 1.26 g (85%) of all-racemic α-tocopherol succinate as viscous yellow oil. IR (neat, thin film) υ (br), 2927, 1755, 1715, 1461, 1377, 1151, 1109 cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ (12H, m), (24H, m), (2 H, m), (±) Succinic acid mono-[2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-tridecyl)- chromone-6-yl) ester (all racemic-α-tocopheryl succinate, Rac-VES). Racemic α-tocopherol (1.20 g, 2.79 mmol) was dissolved in anhydrous CH 2 Cl 2 (15 ml) and was treated with succinic anhydride (0.28 g, 2.79 mmol, 1 equiv) and 4-dimethylaminopyridine (DMAP, 0.34 g, 2.79 mmol, 1 equiv) at 23 C. After being stirred for 3 days, the mixture was diluted with Et 2 (60 ml) and aqueous HCl (3 N, 20 ml) and the organic and aqueous layers were separated. The aqueous layer was extracted with Et 2 (30 ml). The combined organic layers were dried over 1.97 (3H, s), 2.01 (3H, s), 2.08 (3H, s), (2H, m), (2H, m), (2H, m); 13 C NMR (CDCl 3, 75.5 MHz) δ 11.8, 12.0, 12.9, 19.68, 19.74, 20.6, 21.0, 22.6, 22.7, 24.4, 24.8, 28.0, 28.6, 28.9, 31.1, 32.7, 32.8, 37.3, 37.4, 37.5, 39.4, 75.1, 117.4, 123.0, 124.9, 126.7, 140.4, 149.5, 170.8, 177.4; HRMS (ESI) calculated for C 33 H 55 5 [M+H] + : , found [2,5,7,8-Tetramethyl-2R-(4R,8R,12-trimethyl-tridecyl)-chroman-6-yloxy]-butyric acid (RRR-α-tocopheryl succinate ether analog, RRR-TSE). RRR-TSE was produced as previously report (15, 16). 3-[2,5,7,8-Tetramethyl-2R-(4R,8R,12-trimethy-tridecyl)-3,4-dihydro-2H-chroman- 6-yloxy]-propane-1-sulfonic acid (R,R,R-α-Tocopheryloxypropyl sulfonic acid, RRR- VEPSA). RRR-α Tocopherol (RRR-Toc) (1.00 g, 2.32 mmol), and NaH (0.111 g, 4.64 mmol), 3
4 were combined in a 25 ml two neck round bottom flask in THF (20 ml, 0.12 M) at 0 o C under argon. 1, 3-Propane sultone (0.34 g, 2.79 mmol) was added to the reaction mixture after stirring at room temperature for 50 min. The reaction was then heated at reflux for 24 h. Upon completion the reaction was quenched with conc. HCl, extracted with a 3:1 mixture of EtAc: iprh, washed with acidified brine, then dried over anhydrous Na 2 S 4. The organic layer was then concentrated in vacuo, to form a brown solid which was then subjected to flash chromatography using 1 1 / 2 inch silica gel [gradient of EtAc: hexane from (1: 4) to 100% EtAc] followed by EtAc:HAc (20 : 1)], to yield (0.792g, 60 %) as a tan / brown waxy solid. [α] 25 D = (c 1.0, chloroform); λ max /nm (UV/Vis, chloroform): 288; (UV/Vis, ethanol): 212, 288; R f ( 1:1 EtAc: i-prh): 0.2; IR (neat, thin film) υ 2925 (s), 1461 (m), 1376 (m), 1187 (s), 1091 (m), 1056 (s) (m) cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (12 H, m), (18 H, m), 1.26 (3 H, s), (4 H, m), (2 H, m), 2.05 (3 H, s), 2.08 (3 H, s), 2.11 (3 H, s), 2.36 (2 H, m), 2.53 (2 H, m), 3.48 (2 H, m), 3.78 (2 H, m,); 13 C NMR (75.5 MHz, CDCl 3 ) δ 11.7, 11.8, 12.7, 19.6, 19.7, 20.6, 21.0, 22.6, 22.7, 23.5, 24.5, 24.8, 25.2, 28.0, 29.7, 31.3, 32.7, 32.8, 37.3, 37.5, 37.6, 39.4, 40.4, 49.0, 70.8, 74.7, 117.4, 122.8, 125.6, 127.6, 147.6, 147.9; HRMS (ESI) for C 32 H 55 Na 2 5 S [M + 2Na + - H + ] + calculated , found [2,5,7,8-Tetramethyl-2-(4,8,12-trimethy-tridecyl)-3,4-dihydro-2H-chroman-6- yloxy]-propane-1-sulfonic acid (Rac-α-Tocopheryloxypropyl sulfonic acid, Rac-VEPSA). All racemic α-tocopherol (Rac-Toc) (1.01 g, 2.32 mmol) was converted to all racemic VEPSA (1.32 g, 99%) using the same procedure as used for the synthesis of R,R,R-VEPSA. All racemic VEPSA was isolated as brown waxy solid. R f (1:1 EtAc: iprh): 0.2; IR (neat, thin film) υ 2925 (s), 1460 (m), 1376 (m), 1190 (s), 1092 (m), 1056 (s), 739 (s); 1 H NMR (300 4
5 MHz, CDCl 3 ) δ (12 H, m), (18 H, m), 1.26 (3 H, s), (4 H, m), (2 H, m), 1.97 (3 H, s), 1.98 (3 H, s), 2.01 (3 H, s), 2.30 (2 H, m), 2.43 (2 H, m), 3.34 (2 H, m), 3.63 (2 H, m); 13 C NMR (75.5 MHz, CDCl 3 ) δ 11.6, 12.6, 19.6, 19.7, 19.8, 20.5, 21.1, 22.6, 22.7, 23.1, 24.5, 24.8, 25.7, 28.0, 29.7, 31.3, 32.8, 37.3, 37.5, 39.4, 40.9, 48.6, 71.1, 74.4, 117.1, 122.5, 125.6, 127.6, 147.5, 147.9; HRMS (ESI) for [M + H] + C 32 H 57 5 S: calculated , found [2,5,7,8-Tetramethyl-2R-(4R,8R,12-trimethyl-tridecyl)-3,4-dihydro-2H-chroman- 6-yloxy]-butane-1-sulfonic acid (R,R,R-α-Tocopheryloxybutyl sulfonic acid, RRR- VEBSA). RRR-α Τocopherol (RRR-Toc) (1.00 g, 2.32 mmol), and NaH (0.111 g, 4.64 mmol), were combined in a 25 ml two neck round bottom flask in THF (20 ml, 0.12 M) at 0 0 C under argon. 1, 4-Butane sultone (0.38 g, mmol) was added to the reaction mixture after stirring at room temperature for 50 min. The reaction was refluxed for 24 h. Upon completion, the reaction was quenched with conc. HCl, extracted with a 3:1 mixture of EtAc: iprh, washed with acidified brine, then dried over anhydrous Na 2 S 4. The crude organic layer was then concentrated, using a rotovap, to form a brown solid. This was then subjected to flash chromatography using 1 1 / 2 inch silica gel [gradient of EtAc: Hexane from (1: 4) to 100% EtAc] followed by EtAc : HAc (20 : 1)], to yield (1.02g, 76%) as light brown waxy solid. [α] 25 D = ( c 1.0, chloroform); λ max /nm (UV/Vis, chloroform): 288, (UV/Vis, ethanol): 214, 276; R f (1:1 EtAc: iprh): 0.19; IR (neat, thin film) υ 2924 (s), 1459 (m), 1377 (m), 1169 (s), 1090 (m), 1054 (s) cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (12 H, m), (20 H, m), 1.27 (3 H, s), (4 H, m), (2 H, m), (2 H, m), 2.03 (3 H, s), 2.06 (3 H, s), 2.09 (3 H, s), 2.50 (2 H, m), 3.16 (2 H, m), (2 H, m); 13 C NMR (75.5 MHz, CDCl 3 ) δ 11.7, 11.8, 12.7, 19.6, 19.7, 20.6, 21.0, 21.4, 22.6, 22.7, 23.4, 24.5, 5
6 24.8, 28.0, 29.2, 31.3, 32.7, 32.8, 37.3, 37.5, 37.5, 37.6, 39.4, 40.6, 51.3, 72.2, 74.6, 117.3, 122.6, 125.7, 127.6, 147.7, 148.1; HRMS (EI) for C 33 H 58 5 S [M] + calculated , found [2,5,7,8-Tetramethyl-2-(4,8,12-trimethyl-tridecyl)-3,4-dihydro-2H-chroman-6- yloxy]-butane-1-sulfonic acid (Rac-α-Tocopheryloxybutyl sulfonic acid, Rac-VEBSA). All racemic α-tocopherol (1.00 g, 2.32 mmol) was converted to all-racemic VEBSA (1.03 g, 76%) using the same procedure as for R,R,R-VEBSA. All racemic VEBSA was isolated as a brown solid. R f (1:1 EtAc: iprh): 0.2; IR (neat, thin film) υ 2925 (s), 1460 (m), 1377 (m), 1188 (s), 1090 (m), 1054 (s), 736 (w) cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ (12 H, m), (23 H, m), (4 H, m), (2 H, m), (2 H, m), (9 H, m), 2.44 (2 H, m), 3.08 (2 H, m), 3.54 (2 H, m); 13 C NMR (75.5 MHz, CDCl 3 ) δ 11.7, 11.8, 12.7, 19.6, 19.7, 20.6, 21.0, 21.4, 22.6, 22.7, 23.4, 24.5, 24.8, 28.0, 29.2, 31.3, 32.7, 32.8, 37.3, 37.47, 37.51, 37.6, 39.4, 40.6, 51.3, 72.2, 74.6, 117.3, 122.6, 125.7, 127.6, 147.7, 148.1; HRMS (ESI) for [M + 2Na H + ] + C 33 H 57 Na 2 5 S + : calculated , found [2,5,7,8-Tetramethyl-2R-(4R,8R,12-trimethyl-tridecyl)3,4-dihydro-2H-chroman- 6-yloxy]-propylphosphonic acid (R,R,R-α-Tocopheryloxypropyl phosphonic acid, RRR- VEPPA). RRR-α-Tocopheryloxypropyl diethylphosphonate (0.177 g, mmol), and 9 N HCl (2 ml) were combined in a 25 ml round bottom flask. The reaction mixture was refluxed at C for 24 h. Upon completion the reaction was extracted with CH 2 Cl 2 and dried (Na 2 S 4 ). Concentration in vacuo yielded RRR-VEPPA as a brown oil ( g, 89%) that was not subjected to flash chromatography due to its highly polar nature. [α] 25 D = (c 1.0, chloroform); λ max /nm (UV/Vis, chloroform): 282, (UV/Vis, ethanol): 214, 286; R f (1:1 EtAc: iprh): 0.14; IR (neat, thin film) υ 2924 (s), 2358 (w), 1459 (m), 1259 (m), 1088 (s), 1015 (s), 6
7 799 (s); 1 H NMR (400 MHz, CDCl 3 ) δ (12 H, m), (25 H, m), 1.25 (3 H, s), (2 H, m), 2.06 (3 H, s), 2.09 (3 H, s), 2.14 (3 H, s), 2.24 (2 H, s), (2 H, m), 3.69 (2 H, m); 13 C NMR (75.5 MHz, CDCl 3 ) δ 11.8, 11.9, 12.7, 19.7, 19.8, 20.6, 21.0, 22.6, 22.7, 23.2, 23.8, 24.4, 24.8, 28.0, 29.7, 31.3, 32.7, 32.8, 37.3, 37.5, 37.5, 39.4, 40.2, 72.2, 74.8, 117.5, 122.9, 125.8, 127.7, 129.3, 147.9, 147.9; HRMS (ESI) for C 32 H 58 5 P + [M + H] + : calculated , found [2,5,7,8-Tetramethyl-2R-(4R,8R,12-trimethyl-tridecyl)3,4-dihydro-2H-chroman- 6-yloxy]-propylphosphonic acid (R,R,R-α-Tocopheryloxypropyl phosphonic acid, RRR- VEPPA). RRR-α-Tocopheryloxypropyl diethylphosphonate (0.177 g, mmol), and 9 N HCl (2 ml) were combined in a 25 ml round bottom flask. The reaction mixture was refluxed at C for 24 h. Upon completion the reaction was extracted with CH 2 Cl 2 and dried (Na 2 S 4 ). Concentration in vacuo yielded RRR-VEPPA as a brown oil ( g, 89%) that was not subjected to flash chromatography due to its highly polar nature. [α] 25 D = (c 1.0, chloroform); λ max /nm (UV/Vis, chloroform): 282, (UV/Vis, ethanol): 214, 286; R f (1:1 EtAc: iprh): 0.14; IR (neat, thin film) υ 2924 (s), 2358 (w), 1459 (m), 1259 (m), 1088 (s), 1015 (s), 799 (s); 1 H NMR (400 MHz, CDCl 3 ) δ (12 H, m), (25 H, m), 1.25 (3 H, s), (2 H, m), 2.06 (3 H, s), 2.09 (3 H, s), 2.14 (3 H, s), 2.24 (2 H, s), (2 H, m), 3.69 (2 H, m); 13 C NMR (75.5 MHz, CDCl 3 ) δ 11.8, 11.9, 12.7, 19.7, 19.8, 20.6, 21.0, 22.6, 22.7, 23.2, 23.8, 24.4, 24.8, 28.0, 29.7, 31.3, 32.7, 32.8, 37.3, 37.5, 37.5, 39.4, 40.2, 72.2, 74.8, 117.5, 122.9, 125.8, 127.7, 129.3, 147.9, 147.9; HRMS (ESI) for C 32 H 58 5 P + [M + H] + : calculated , found [2,5,7,8-Tetramethyl-2R-(4R,8R,12-trimethyl-tridecyl)-3,4-dihydro-2H-chromen- 6-yloxy]-butylphosphonic acid (RRR-α-Tocopheryloxybutyl phosphonic acid, RRR- 7
8 VEBPA). Two ml 9 N HCl was added to a solution of approximately 0.5 ml acetone and RRRα-tocopheryloxybutyl diethylphosphonate ( g, mmol) in a 25 ml round bottom flask. The reaction mixture was refluxed at 100 C for 24 h. Upon completion the reaction was extracted with CH 2 Cl 2 and dried (Na 2 S 4 ). Concentration of product in vacuo gave RRR- VEBPA as a brown oil ( g, 73%). λ max /nm (UV/Vis, chloroform): 282, (UV/Vis, ethanol): 214, 286; R f (1:1 EtAc: iprh): 0.16; IR (neat, thin film) δ 2925 (s), 2357 (s), 1460 (m), 1378 (m), 1259 (m), 1090 (m), 1090 (m), 805 (m); 1 H NMR (400 MHz, CDCl 3 ) δ (12 H, m), (27 H, m), 1.26 (3 H, s), (4 H, m), 2.07 (3 H, s), 2.10 (3 H, s), 2.15 (3 H, s), (2 H, m), 3.64 (2 H, m); 13 C NMR (75.5 MHz, CDCl 3 ) δ 11.8, 11.9, 12.7, 14.1, 19.65, 19.74, 20.7, 21.0, 22.6, 22.7, 23.8, 24.5, 24.8, 27.1, 28.0, 29.4, 29.7, 30.0, 31.3, 31.9, 32.8, 37.3, 37.5, 39.4, 40.2, 74.7, 117.5, 122.8, 125.7, 127.7, 147.8, 147.9; HRMS (ESI) for [M + H] + C 33 H 60 5 P + : calculated , found Detection of VEBSA and VES VEBSA and VES were detected by the HPLC using a reverse phase c-18 column. The mobile phase was 10 mm ammonium acetate in methanol. VEBSA and VES were detected via UV-Vis at 280 nm wavelength and 220 nm wavelength, respectively. The retention time for both VEBSA and VES was ~350 seconds. The extraction and quantification of VEBSA and VES We extracted VEBSA or VES from 300 μl serum by adding 200 μl 6M HCl and 200 μl ethyl acetate. The sample was then vortexed and centrifuged for 1 min at 12,000 rpm. The organic layer was separated and filtered through a c-18 sep-pack column filter and then 8
9 concentrated. This sample was then re-dissolved in 40 μl of methanol and detected on the HPLC as described above. The area under the curve was then determined and the standard calibration curve was used to determine the concentration of VEBSA (or VES) in methanol. Standard solutions of 0 μm, 20 μm, 30 μm, 50 μm, 100 μm, 150 um, and 200 μm of VEBSA (or VES) were prepared in methanol and chromatographed on the HPLC. Each sample was run three times. The area under the curve (AUC) for each sample was then calculated using GraphPad Prism software ver A standard calibration curve was then plotted based on the average of the AUC of VEBSA (or VES) versus the standard concentrations. 9
10 Supplemental Figure Legend: Supplemental Figure 1: The HPLC detection graph of detection of VEBSA and VES in pooled mouse serum collected from mice after oral administration of VEBSA, VES or mock for one month. Detection of VEBSA in pooled mouse serum collected from mice after oral administration of VEBSA (A) and mock (B). Detection of VES in pooled mouse serum collected from mice after oral administration of VES (C) and mock (D). The area under the curve (AUC) for each sample was then calculated using GraphPad Prism software ver to determine the concentration of VEBSA (or VES) in methanol. Each sample was run three times. A B C D 10
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 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 informationTetrahydrofuran (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 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. 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 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 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 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 informationSupporting 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 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 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 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 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 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
An Improved ynthesis of the Pyridine-Thiazole Cores of Thiopeptide Antibiotics Virender. Aulakh, Marco A. Ciufolini* Department of Chemistry, University of British Columbia 2036 Main Mall, Vancouver, BC
More informationPhil S. Baran*, Jeremy M. Richter and David W. Lin SUPPORTING INFORMATION
Direct Coupling of Pyrroles with Carbonyl Compounds: Short, Enantioselective Synthesis of (S)-Ketorolac Phil S. Baran*, Jeremy M. Richter and David W. Lin SUPPRTIG IFRMATI General Procedures. All reactions
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 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 informationSupplementary 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 informationCompound 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 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
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 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 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 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 Information for: Phosphonates
Supporting Information for: A Room-Temperature Alternative to the Arbuzov Reaction: the Reductive Deoxygenation of Acyl Phosphonates Sean M. A. Kedrowski and Dennis A. Dougherty* Division of Chemistry
More informationSupporting 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 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 informationSupporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B
Supporting Information Expeditious Construction of the DEF Ring System of Thiersinine B Masaru Enomoto and Shigefumi Kuwahara* Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural
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 informationA fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media
Supplementary Information A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Weiwei Wang and Quanrui Wang* Department of Chemistry,
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 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 informationSupplementary Material (ESI) for Chemical Communication
Supplementary Material (ESI) for Chemical Communication Syntheses and Characterization of Polymer-Supported Organotrifluoroborates: Applications in Radioiodination Reactions Li Yong; Min-Liang Yao; James
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 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 informationElectronic 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 informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
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 informationAsymmetric Synthesis of Hydrobenzofuranones via Desymmetrization of Cyclohexadienones using the Intramolecular Stetter Reaction
Asymmetric Synthesis of Hydrobenzofuranones via Desymmetrization of Cyclohexadienones using the Intramolecular Stetter Reaction Qin Liu and Tomislav Rovis* Department of Chemistry, Colorado State University
More information1G (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 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 informationSUPPLEMENTARY INFORMATION
Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using
More informationSupplementary 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 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 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 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 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 information(A) Effect of I-EPI-002, EPI-002 or enzalutamide on dexamethasone (DEX, 10 nm)
Supplemental Figure Legends Supplemental Figure 1. (A) Effect of I-EPI-002, EPI-002 or enzalutamide on dexamethasone (DEX, 10 nm) induced GR transcriptional activity in LNCaP cells that were transiently
More informationSupporting 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 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 informationFluorescent probe for Lewisite Simulant
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 2016 Supporting information (New
More informationAmelia A. Fuller, Bin Chen, Aaron R. Minter, and Anna K. Mapp
Supporting Information for: Concise Synthesis of b-amino Acids via Chiral Isoxazolines Amelia A. Fuller, Bin Chen, Aaron R. Minter, and Anna K. Mapp Experimental Section General. Unless otherwise noted,
More informationSupporting 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 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. Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation.
Supporting information Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation Saithalavi Anas, Alex Cordi and Henri B. Kagan * Institut de Chimie
More informationEnantioselective Synthesis of Fused Heterocycles with Contiguous Stereogenic Centers by Chiral Phosphoric Acid-Catalyzed Symmetry Breaking
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Enantioselective Synthesis of Fused Heterocycles with Contiguous Stereogenic Centers by Chiral
More informationN-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]
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 An L-proline Functionalized Metallo-organic Triangle as Size-Selective Homogeneous Catalyst for Asymmertry Catalyzing Aldol Reactions Xiao Wu, Cheng He, Xiang Wu, Siyi Qu and Chunying
More informationSupporting 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 informationExperimental details
Supporting Information for A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyx) ligand Hideki Shimizu 1,2, Jeffrey C. Holder 1 and Brian M. Stoltz* 1 Address:
More informationBlock: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection
Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and
More informationwith EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15
2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0
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 informationSupporting 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 informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Complete Switch of Migratory Aptitude in Aluminum-Catalyzed 1,2-Rearrangement of Differently α,α-disubstituted α-siloxy Aldehydes Kohsuke hmatsu,
More informationSilver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous
More informationSupplementary Materials
Supplementary Materials ORTHOGOALLY POSITIOED DIAMIO PYRROLE- AD IMIDAZOLE- COTAIIG POLYAMIDES: SYTHESIS OF 1-(3-SUBSTITUTED-PROPYL)-4- ITROPYRROLE-2-CARBOXYLIC ACID AD 1-(3-CHLOROPROPYL)-4- ITROIMIDAZOLE-2-CARBOXYLIC
More informationSupporting 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 informationRing-Opening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols
Ring-pening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols Jumreang Tummatorn, and Gregory B. Dudley, * Department of Chemistry and Biochemistry, Florida State University,
More informationSupplementary Methods
Supplementary Methods Synthesis overview 4 a-c C 5 TBS d H 2 TBS 6 H 2 H 2 (Boc) 2 e f-h i Br TBS TBS TBS 7 8 9 j,k (Boc) 2 l H 2 H H 10 fmk (1) Scheme 1. Reagents and conditions: a. malononitrile, MeH,
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 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
UPPRTING INFRMATIN Application of a Rhodium-Catalyzed Addition/Cyclization equence Toward the ynthesis of Polycyclic eteroaromatics Nai-Wen Tseng and Mark Lautens* Davenport Laboratories, Chemistry Department,
More informationRational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+
Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Weimin Xuan, a Chen Chen, b Yanting Cao, a Wenhan He, a Wei Jiang, a Kejian Li, b* and Wei
More informationRecyclable 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 informationSynthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition
Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Sonia Amel Diab, Antje Hienzch, Cyril Lebargy, Stéphante Guillarme, Emmanuel fund
More informationA contribution from the Department of Chemistry, Washington University, Campus Box 1134, One Brookings Drive, Saint Louis, Missouri 63130
BENZOTETRAMISOLE (BTM): A REMARKABLY ENANTIOSELECTIVE ACYL TRANSFER CATALYST Vladimir B. Birman* and Ximin Li A contribution from the Department of Chemistry, Washington University, Campus Box 1134, One
More informationElectronic 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 informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany rganocatalytic Conjugate Addition of Malonates to a,ß-unsaturated Aldehydes: Asymmetric Formal Synthesis of (-)-Paroxetine, Chiral Lactams
More informationSupporting Information for: Using a Lipase as a High Throughput Screening Method for Measuring the Enantiomeric. Excess of Allylic Acetates
Supporting Information for: Using a Lipase as a High Throughput Screening Method for Measuring the Enantiomeric Excess of Allylic Acetates M. Burak Onaran and Christopher T. Seto* Department of Chemistry,
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
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 informationPoly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 24 Supporting Information Poly(4-vinylimidazolium)s: A Highly Recyclable rganocatalyst Precursor
More informationFigure S1 - Enzymatic titration of HNE and GS-HNE.
Figure S1 - Enzymatic titration of HNE and GS-HNE. Solutions of HNE and GS-HNE were titrated through their reduction to the corresponding alchools catalyzed by AR, monitoring the decrease in absorbance
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise
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 informationA biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed-bed microreactor
A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed-bed microreactor Andrew Bogdan 1 and D. Tyler McQuade 2, * Address: 1 Department of Chemistry and Chemical Biology, Cornell
More informationMetal-free general procedure for oxidation of secondary amines to nitrones
S1 Supporting information Metal-free general procedure for oxidation of secondary amines to nitrones Carolina Gella, Èric Ferrer, Ramon Alibés, Félix Busqué,* Pedro de March, Marta Figueredo,* and Josep
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 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 informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Rapid and sensitive detection of acrylic acid using a novel fluorescence
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 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 informationSUPPLEMENTARY INFORMATION
doi:10.1038/nature24451 Chemical synthesis of USP7 compounds General 1 H, 13 C and 19 F nuclear magnetic resonance (NMR) spectra were obtained on either Bruker or Varian spectrometers at 300 or 400 MHz,
More informationEur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 ISSN X SUPPORTING INFORMATION
Eur. J. rg. Chem. 2006 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 ISSN 1434 193X SUPPRTING INFRMATIN Title: Ruthenium(II)-Catalyzed Cyclization of xabenzonorbornenes with Propargylic Alcohols:
More informationElectronic Supplementary Information. An Ultrafast Surface-Bound Photo-active Molecular. Motor
This journal is The Royal Society of Chemistry and wner Societies 2013 Electronic Supplementary Information An Ultrafast Surface-Bound Photo-active Molecular Motor Jérôme Vachon, [a] Gregory T. Carroll,
More information