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Title: First stereoselective total synthesis of (3R, 3aS, 6aR)-hexahydrofuro[2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutyl phenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl-carbamate (diastereomer of Darunavir)
Authors: Babu, Kilaru Ravendra
Rao, Valasani Koteswara
Sudhakar, Yellapu
Raju, Chamarthi Naga
Keywords: Stereoselective
Darunavir diastereomer
D-phenyl alanine
Anti HIV-activity
Issue Date: Jun-2012
Publisher: NISCAIR-CSIR, India
Abstract: The stereoselective novel synthesis of (3R,3aS,6aR)-hexahydrofuro [2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutyl phenyl sulfonamido)-3-hydroxy-1-phenylbutan-2-yl-carbamate, has been accomplished in situ from the intermediate 4-amino-N-((2S,3R)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzen sulfonamide 7. This reaction gives 88% yield, with an optical purity of 99.5% and diastereomeric purity of 99% for chiral alcohol 8.
Page(s): 849-854
CC License:  CC Attribution-Noncommercial-No Derivative Works 2.5 India
ISSN: 0975-0983(Online); 0376-4699(Print)
Source:IJC-B Vol.51B(06) [June 2012]

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