SYNTHESIS OF 1,6-ANHYDRO-2-CHLORO-2,3,4-TRIDEOXY-BETA-D-ERYTHRO-HEX-3-ENOPYRANOSE AND ITS STEREOSPECIFIC SN2' SUBSTITUTION

被引：6

作者：

MATSUMOTO, M

ISHIKAWA, H

SOYA, Y

OZAWA, T

机构：

[1] Department of Materials Science, Kanagawa University Tsuchiya, Hiratsuka, Kanagawa

来源：

HETEROCYCLES | 1994年 / 38卷 / 11期

关键词：

D O I：

10.3987/COM-94-6864

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chlorination of 1,6-anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose (2) with SOCl2 and pyridine gives predominantly 1,6-anhydro-2-chloro-beta-D-erythro-hex-3-enopyranose (3). The chloride (3) takes place exclusively the suprafacial SN2' substitution with a variety of nucleophiles in DMF. ''Cerny epoxides'' are conveniently synthesized by using the reaction of 3 with PhCH2ONa.

引用

页码：2377 / 2381

页数：5

共 8 条

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