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Title: First stereoselective total synthesis of (3<i style="">R</i>, 3a<i style="">S</i>, 6a<i style="">R</i>)-hexahydrofuro[2,3-<i>b</i>]furan-3-yl (2<i style="">R</i>,3<i style="">S</i>)-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 (3<i style="">R</i>,3a<i style="">S</i>,6a<i style="">R</i>)-hexahydrofuro [2,3<i style="">-b</i>]furan-3-yl (2<i style="">R</i>,3<i style="">S</i>)-4-(4-amino-N-isobutyl phenyl sulfonamido)-3-hydroxy-1-phenylbutan-2-yl-carbamate, has been accomplished <i>in situ</i> from the intermediate 4-amino-N-((2<i style="">S</i>,3<i style="">R</i>)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzen sulfonamide <b>7</b>. This reaction gives 88% yield, with an optical purity of 99.5% and diastereomeric purity of 99% for chiral alcohol <b>8</b>.
Description: 849-854
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(06) [June 2012]

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