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Ct. The solution cannot be very easily converted to any known structure.
Ct. The solution cannot be very easily converted to any identified structure.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Procedure for the -Amination of the AldehydeA modification of reported procedure38 was made use of. Dibenzyl azodicarboxylate (90 , 1.29 g, three.9 mmol) and proline (70 mg, 0.six mmol) in MeCN (ten mL) have been cooled down to -3 . The aldehyde (1.02 g three.0 mmol) was then added as well as the GM-CSF Protein Species mixture was stirred at -3 for 2 h. The reaction was steadily warmed to 20 within ca. 1 h. The mixture was then cooled to 0 , treated with MeOH (3 mL) and NaBH4 (240 mg, 6.0 mmol) and was stirred for five min at 0 . The reaction was quenched by 1M KHSO4. The aqueous resolution was extracted with EtOAc 3 occasions. The combined organic layers were dried with MgSO4, and concentrated in vacuo. Purification in the residue by flash chromatography on silica gel, eluting with 15 EtOAchexanes gave the desired alcohol as white foamy strong.J Org Chem. Author manuscript; offered in PMC 2014 December 06.Khumsubdee et al.PageNIH-PA Author ManuscriptDibenzyl 1-((2R,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3-methylbutan-2yl)hydrazine-1,2-dicarboxylate (anti-9) The compound was ready as outlined by the common -amination process catalysed by (R)-Proline. Purification by flash chromatography afforded anti-9 as a white foamy strong (1.54 g, 80 isolated yield). 1H NMR (400 MHz, CDCl3) 7.70 7.67 (m, 4H), 7.50 7.27 (m, 16H), 6.85 (d, J = 31.1 Hz, 1H), 5.37 five.ten (m, 4H), 4.45 four.12 (m, 2H), 3.80 3.41 (m, 4H), 1.95 1.66 (m, 1H), 1.12 1.09 (m, 9H), 0.99 0.88 (m, 3H); 13C NMR (one hundred MHz, CDCl3) 159.1, 157.4, 135.six, 133.3, 133.two, 129.6, 129.eight, 128.7, 128.six, 128.two, 127.9, 127.eight, 127.7, 68.62, 65.88, 65.56, 60.37, 35.six, 26.9, 19.3, 15.1. IR (CH2Cl2) n (cm-1) 3356, 3032, 2928, 1717, 1454, 1408, 1265, 1227, 1111, 1057. HRMS (ESI, TOF): mz = 641.3078, calcd For C37H45N2O6Si [MH] 641.3047. The diastereoselectivity was 1.0:13, determined by Chiral HPLC (Chiralcel OD, HexiPrOH 93:7, 1 mLmin, 25 ), tr ten.3 min (minor IL-7 Protein site diastereomer), tr 14.4 min (major diastereomer).NIH-PA Author Manuscript NIH-PA Author ManuscriptDibenzyl 1-((2S,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3-methylbutan-2yl)hydrazine-1,2-dicarboxylate (syn-9) The compound was prepared in accordance with the standard -amidation procedure catalysed by (S)-Proline. Purification by flash chromatography afforded syn-9 as a white foamy solid (1.63 g, 85 isolated yield). 1H NMR (400 MHz, CDCl3) 7.69 7.62 (m, J = 13.5, six.six Hz, 4H), 7.50 7.24 (m, 16H), 6.96 (s, 1H), 5.30 five.22 (m, 3H), 5.13 (dd, J = 12.1, 9.6 Hz, 1H), 4.36 4.16 (m, 2H), three.86 3.70 (m, 2H), 3.59 three.44 (m, 2H), 1.80 (br, 1H), 1.11 1.08 (m, 9H), 0.93 0.90 (m, 3H); 13C NMR (100 MHz, CDCl3) 158.six, 158.two, 156.eight,J Org Chem. Author manuscript; obtainable in PMC 2014 December 06.Khumsubdee et al.Page156.five, 135.9, 135.six, 135.five, 135.4, 133.0, 130.1, 129.9, 128.6, 128.five, 128.1, 127.9, 127.8, 68.three, 64.0, 63.two, 60.6, 35.five, 27.0, 19.two, 14.9. IR (CH2Cl2) n (cm-1) 3356, 3032, 2959, 1724, 1470, 1408, 1261, 1223, 1111, 1053. HRMS (ESI, TOF): mz = 641.3063 calcd For C37H45N2O6Si [MH] 641.3047. The diastereoselectivity was 62:1.0, determined by Chiral HPLC (Chiralcel OD, HexiPrOH 93:7, 1 mLmin, 25 ), tr 10.two min (minor diastereomer), tr 14.three min (significant diastereomer).NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Procedure for the Hydrogenolysis and Benzylation with the AlcoholTo Raney ickel ( 0.3 g, prewashed with.