Reactions of per-O-acetylglucosyl isothiocyanate with carbon bases.: A new method for the stereocontrolled syntheses of nucleosides and glucosylaminothiophenes

被引：24

作者：

Fuentes, J ^{[1
]}

Molina, JL ^{[1
]}

Pradera, MA ^{[1
]}

机构：

[1] Univ Seville, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(98)00243-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylisothiocyanate 5 with diethyl malonate in a basic medium gave the corresponding glucopyranosyl thioamide without significant deacetylation. This thioamide in solution presents Z-anti as the sole configuration. Reactions of 5 with carbanions which have an ethoxycarbonyl group are a way to prepare anomerically pure N-nucleoside derivatives of pyrrole and tetrahydropyridine. Reactions of 5 with carbanions stabilized by one cyano group are used to prepare glucosylamino thiophenes with only the B-configuration. Some other stereochemical aspects of the prepared compounds are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2517 / 2532

页数：16

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