A SHORT SYNTHESIS OF 3(R)-HYDROXY-2(R)-ISOPROPYLTETRAHYDROTHIOPHENE - A PRECURSOR TO A HIGH-AFFINITY P2-LIGAND OF HIV-1 PROTEASE INHIBITORS

被引：9

作者：

KIM, BM

LEE, HY

MUNSON, PM

GUARE, JP

MCDONOUGH, C

机构：

[1] Department of Medicinal Chemistry, Merck Research Laboratories, Merck and Co., Inc., West Point

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 41期

关键词：

D O I：

10.1016/0040-4039(93)88093-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound was synthesized in a 6 step sequence involving an efficient lipase-mediated resolution of racemic 3-hydroxy-2-isopropyltetrahydrothiophene.

引用

页码：6517 / 6520

页数：4

共 16 条

[1] A ROUTE TO ARTIFICIAL GLYCOCONJUGATES AND OLIGOSACCHARIDES VIA ENZYMATICALLY RESOLVED GLYCALS - DRAMATIC EFFECTS OF THE HANDEDNESS OF THE SUGAR DOMAIN UPON THE PROPERTIES OF AN ANTHRACYCLINE DRUG [J].

BERKOWITZ, DB ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4518-4529

[2]

BOLAND W, 1991, SYNTHESIS-STUTTGART, P1049

[3] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[4]

GABOURY MP, 1993, J ORG CHEM, V58, P2173

[5] CYCLIC SULFOLANES AS NOVEL AND HIGH-AFFINITY P-2 LIGANDS FOR HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

THOMPSON, WJ ;

LEE, HY ;

MCKEE, SP ;

MUNSON, PM ;

DUONG, TT ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (07) :924-927

[6] 3-TETRAHYDROFURAN AND PYRAN URETHANES AS HIGH-AFFINITY P2-LIGANDS FOR HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

THOMPSON, WJ ;

MCKEE, SP ;

DUONG, TT ;

LYLE, TA ;

CHEN, JC ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (02) :292-294

[7]

KIM BS, UNPUB

[8] ASYMMETRIC TRANSFORMATIONS CATALYZED BY ENZYMES IN ORGANIC-SOLVENTS [J].

KLIBANOV, AM .

ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :114-120

[9]

Schaefer J.P., 1967, ORG REACT, V15, P1

[10]

SCHWARTZ A, 1991, ORG SYNTH, V61, P1

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