N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters .2. Applications in peptide synthesis.

被引：14

作者：

Barton, DHR

Ferreira, JA

机构：

[1] Department of Chemistry, Texas A and M University, College Station

来源：

TETRAHEDRON | 1996年 / 52卷 / 28期

关键词：

D O I：

10.1016/0040-4020(96)00488-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-hydroxypyridine-2(1H)-thione derivatives of two urethane-protected alpha-amino acids readily reacted with free alpha-amino acid esters or the corresponding benzenesulfenamides to give simple dipeptides in reasonable yields. The benzenesulfenamides are the reagents of choice since they allowed for neutral reaction conditions and exhibited superior reactivity in sterically demanding instances. The atom-economical reaction between a Barton PTOC ester and a benzenesulfenamide afforded products of synthetic and biological value and proceeds in a concerted fashion, thereby maintaining chirality in couplings involving optically active alpha-amino acid residues. Copyright (C) 1996 Elsevier Science Ltd

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收藏

页码：9367 / 9386

页数：20

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