From the residue by flash chromatography on silica gel, eluting with 10 20 EtOAc/hexanes gave 11 as a white foamy solid. To a remedy of RuCl3 (29 mg, 0.14 mmol) and NaIO4 (2.95 g, 13.eight mmol) in water was added 11 (800 mg, 1.38 mmol). The mixture was stirred at 23 for two h, and thenJ Org Chem. Author manuscript; available in PMC 2014 December 06.Khumsubdee et al.Pageadded MeOH (two mL). The reaction was stirred until solid precipitation occurred. The strong was filtered on Celite and washed it with EtOAc. 1 M KHSO4 (three mL) was added for the filtrate. Then, the aqueous phase was extracted by EtOAc. The combined organic layers have been dried with MgSO4, and concentrated in vacuo. Purification of your residue by flash chromatography on silica gel, eluting with 15 50 EtOAc/hexanes gave the desired acid 12 as a white foamy solid.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript(9H-Fluoren-9-yl)methyl ((2S,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3methylbutan-2-yl)carbamate (syn-11) Purification by flash chromatography afforded syn-11 as a white foamy solid (1.28 g, 98 yield in two measures). 1H NMR (400 MHz, CDCl3) 7.86 7.74 (m, 6H), 7.66 (dd, J = 7.3, three.six Hz, 2H), 7.55 7.40 (m, 8H), 7.34 (t, J = 7.4 Hz, 2H), six.05 (d, J = 6.7 Hz, 1H), four.50 (d, J = six.5 Hz, 2H), 4.28 (t, J = 6.8 Hz, 1H), 3.93 3.74 (m, 4H), 3.69 (dd, J = 10.four, 4.5 Hz, 1H), 3.31 (br, 1H), two.05 (br, 1H), 1.19 (s, 9H), 1.13 (d, J = 6.7 Hz, 3H); 13C NMR (100 MHz, CDCl3) 157.39, 144.1, 141.40, 135.7, 132.9, 130.0, 127.9, 127.7, 127.1, 125.two, 120.0, 66.9, 66.0, 64.6, 56.7, 47.4, 35.7, 27.0, 19.2, 15.three. IR (CH2Cl2) n (cm-1) 3402, 3067, 2928, 1701, 1508, 1450, 1327, 1227, 1111, 1042. HRMS (ESI, TOF): m/z = 580.2874, calcd For C36H42NO4Si [M+H]+ 580.2883.(9H-Fluoren-9-yl)methyl ((2R,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3methylbutan-2-yl)carbamate (anti-11) Purification by flash chromatography afforded anti-11 as a white foamy strong (1.24 g, 95 yield in two methods). 1H NMR (500 MHz, CDCl3) 7.84 7.77 (m, 2H), 7.74 (dd, J = 7.7, 6.7 Hz, 4H), 7.64 (d, J = 7.four Hz, 2H), 7.55 7.39 (m, 8H), 7.33 (td, J = 7.5, 1.0 Hz, 2H), 5.J Org Chem. Author manuscript; offered in PMC 2014 December 06.Khumsubdee et al.Page(d, J = eight.three Hz, 1H), 4.51 4.43 (m, 2H), four.26 (t, J = 6.9 Hz, 1H), three.90 (dd, J = 11.2, four.2 Hz, 1H), three.83 3.80 (m, 1H), three.78 3.69 (m, 2H), three.63 (dd, J = ten.7, 7.two Hz, 1H), three.34 (br, 1H), 2.11 two.10 (m, 1H), 1.15 (s, 9H), 0.97 (d, J = 7.two Hz, 3H); 13C NMR (125 MHz, CDCl3) 156.9, 144.0, 141.4, 135.7, 132.eight, 130.1, 127.9, 127.7, 127.1, 125.1, 120.02, 66.eight, 66.5-Methylcytidine supplier 1, 63.0, 56.3, 47.four, 37.two, 27.0, 19.two, 14.1. IR (CH2Cl2) n (cm-1) 3368, 3067, 2928, 1701, 1512, 1450, 1242, 1111. HRMS (ESI, TOF): m/z = 580.2865, calcd For C36H42NO4Si [M+H]+ 580.(2-Hydroxypropyl)-β-cyclodextrin In stock 2883.PMID:24278086 NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript(2S,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-((tert-butyldiphenylsilyl)oxy)-3methylbutanoic acid (syn-12) Purification by flash chromatography afforded syn-12 as a white foamy strong (0.42 g, 49 yield). 1H NMR (400 MHz, CDCl3) 7.89 7.60 (m, 8H), 7.55 7.29 (m, 10H), six.41 (d, J = 8.4 Hz, 1H), 4.61 4.51 (m, 7H), 4.34 (t, J = 6.9 Hz, 1H), 3.88 (d, J = 8.5 Hz, 1H), three.62 (dd, J = ten.7, five.1 Hz, 1H), 2.49 (m, 1H), 1.25 1.09 (m, 12H); 13C NMR (100 MHz, CDCl3) 177.12, 156.94, 143.9, 141.three, 135.7, 132.6, 130.0, 127.9, 127.7, 127.1, 125.3, 120.0, 67.4, 66.1, 58.1, 47.1, 36.4, 26.9, 19.two, 14.7. IR (CH2Cl2) n (cm-1) 3399, 3067, 2928, 1717,.
