Journal Article
Diastereoselective synthesis of (3r, 3as, 6ar)-hexahydrofuro [2,3-b] furan-3-Yl (2r, 3r)-4-(4-amino-N-isobutylphenylsulfo- namido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (diastereomer of darunavir)
Babu, KR; Rao, VK; Naga Raju, C
(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl(2S,3S)-4-(4-amino-N-isobutylphenylsulfonamido) -3-hydroxy-1-phenylbutan-2-ylcarbamate 4 was synthesised from 4-amino-N-((2S,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfo- namide 3 via N-protected amino alcohol intermeidate 2 while (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-Nisobutylphenylsulfonamido)-3-(((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy)carbonyloxy)-1-phenylbutan-2-yl carbamate 6 was prepared from (3R, 3aS, 6aR)-hexahydrofuro [2,3-b] furan-3-yl 4-nitrophenyl carbonate 3a. The desired drug 4 was obtained with 99 % diastereoselectivity. The spectroscopic analyses performed by NMR, LCMS, UV-Vis, SOR and FT-IR.
(R,S)-Epoxide; Bis-THF phenyl carbonate; Diastereo selectivity; Enantioselctivity; Protease inhibitors; 3,3,6 hexahydrofuro[2,3 b]furan 3 yl 4 (4 amino n isobutylphenylsulfonamido) 3 [(3,3,6 hexahydrofuro[2,3 b]furan 3 yloxy)carbonyloxy] 1 phenylbutan 2 ylcarbamate; 3,3,6 hexahydrofuro[2,3 b]furan 3 yl 4 (4 amino n isobutylphenylsulfonamido) 3 hydroxy 1 phenylbutan 2 ylcarbamate; 3,3,6 hexahydrofuro[2,3 b]furan 3 yl 4 nitrophenyl carbamate; 4 amino n (3 amino 2 hydroxy 4 phenylbutyl) n isobutylbenzenesulfonamide; aminoalcohol; carbamic acid derivative; carbonic acid derivative; darunavir; Human immunodeficiency virus proteinase inhibitor; sulfonamide; unclassified drug; article; asymmetric synthesis; chemical reaction; controlled study; diastereoisomer; drug purity; drug structure; drug synthesis; enantioselectivity; infrared spectroscopy; mass spectrometry; nuclear magnetic resonance spectroscopy; reaction analysis; stereochemistry; stoichiometry; thin layer chromatography; ultraviolet spectroscopy