LARGE-SCALE PREPARATION OF (2S,3S)-N-BOC-3-AMINO-1,2-EPOXY-4-PHENYLBUTANE - A KEY BUILDING-BLOCK FOR HIV-PROTEASE INHIBITORS

被引：47

作者：

BEAULIEU, PL

WERNIC, D

DUCEPPE, JS

GUINDON, Y

机构：

[1] Bio-Méga/Boehringer Ingelheim Research Inc., Laval, Que. H7S 2G5

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 19期

关键词：

D O I：

10.1016/0040-4039(95)00533-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2S,3S)-N-Boc-3-amino-1,2-epoxy-4-phenylbutane is prepared in four steps from commercially available N,N-dibenzyl-L-phenylalaninol. The synthesis is amenable to the preparation of kilogram quantities of enantiomerically pure material.

引用

页码：3317 / 3320

页数：4

共 25 条

[1] AN IMPROVED, CONVENIENT PROCEDURE FOR REDUCTION OF AMINO-ACIDS TO AMINOALCOHOLS - USE OF NABH4-H2SO4 [J].

ABIKO, A ;

MASAMUNE, S .

TETRAHEDRON LETTERS, 1992, 33 (38) :5517-5518

[2] STEREOCONTROLLED SYNTHESIS OF ERYTHRO N-PROTECTED ALPHA-AMINO EPOXIDES AND PEPTIDYL EPOXIDES [J].

ALBECK, A ;

PERSKY, R .

TETRAHEDRON, 1994, 50 (21) :6333-6346

[3]

ANDERSON PC, 1993, Patent No. 560268

[4]

Anh N. T., 1980, TOP CURR CHEM, V88, P145

[5] THE FIRST DIRECT PREPARATION OF CHIRAL FUNCTIONALIZED KETONES AND THEIR SYNTHETIC USES [J].

BARLUENGA, J ;

BARAGANA, B ;

ALONSO, A ;

CONCELLON, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) :969-970

[6] AMINODIOL HIV PROTEASE INHIBITORS .1. DESIGN, SYNTHESIS, AND PRELIMINARY SAR [J].

BARRISH, JC ;

GORDON, E ;

ALAM, M ;

LIN, PF ;

BISACCHI, GS ;

CHEN, P ;

CHENG, PTW ;

FRITZ, AW ;

GREYTOK, JA ;

HERMSMEIER, MA ;

HUMPHREYS, WG ;

LIS, KA ;

MARELLA, MA ;

MERCHANT, Z ;

MITT, T ;

MORRISON, RA ;

OBERMEIER, MT ;

PLUSCEC, J ;

SKOOG, M ;

SLUSARCHYK, WA ;

SPERGEL, SH ;

STEVENSON, JM ;

SUN, CQ ;

SUNDEEN, JE ;

TAUNK, P ;

TINO, JA ;

WARRACK, BM ;

COLONNO, RJ ;

ZAHLER, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1758-1768

[7]

BHISETTI GR, 1994, Patent No. 5639

[8] CHEMISTRY OF ALPHA-HALOMETAL COMPOUNDS - GENERAL METHOD FOR OBTAINING EPOXIDES FROM ALDEHYDES AND KETONES [J].

CAINELLI, G ;

RONCHI, AU ;

TANGARI, N .

TETRAHEDRON, 1972, 28 (11) :3009-&

[9]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[10] INSITU FORMATION AND REACTIONS OF CHLOROMETHYL-LITHIUM UNDER SONOCHEMICAL CONDITIONS [J].

EINHORN, C ;

ALLAVENA, C ;

LUCHE, JL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (05) :333-334

← 1 2 3 →