REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND PHYTOSPHINGOSINE FROM D-GLUCOSAMINE

被引：50

作者：

MURAKAMI, T

MINAMIKAWA, H

HATO, M

机构：

[1] National Institute of Materials and Chemical Research 1-1 Higashi, Tsukuba, Ibaraki

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(00)75806-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

D-erythro-Sphingosine (1) and phytosphingosine (2) have been efficiently synthesized from D-glucosamine by utilizing its whole carbon skeleton and functional groups. In this synthetic route, regioselective alkylation of the epoxy-tosylate 9 was achieved with a copper(I)-catalyzed Grignard reagent to give the key intermediate 10, which was converted to both 1 and 2 via regioselective formation of the iodohydrin 11.

引用

页码：745 / 748

页数：4

共 27 条

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