A NEW SYNTHESIS OF N-ACETYL-4-DEOXY-D-NEURAMINIC ACID

被引：15

作者：

ESTENNE, G ^{[1
]}

SAROLI, A ^{[1
]}

DOUTHEAU, A ^{[1
]}

机构：

[1] INST NATL SCI APPL,DEPT BIOCHIM,CHIM ORGAN LAB,20 AVE ALBERT EINSTEIN,F-69621 VILLEURBANNE,FRANCE

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1991年 / 10卷 / 02期

关键词：

D O I：

10.1080/07328309108543900

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The title compound was prepared in eight steps starting from 2-acetamido-2-deoxy-D-mannose. This commercially available compound was first transformed into known 3-acetamido-1,3-dideoxy-l-nitro-D-glycero-D-galacto-heptitol (2) and then, into 3-acetamido-4,5,6,7-tetra-O-acetyl-2,3-dideoxy-D-manno-heptose (6b). Using a Wittig-Wadsworth-Emmons reaction, aldehyde 6b was then converted into ethyl 5-acetamido-6,7,8,9-tetra-O-acetyl-3,4,5-trideoxy-2-(t-butyldimethyl)silyloxy-D-manno-nonenoate (8). After O-deacetylation, saponification of the ester group and simultaneous deprotection of the silyloxy enol ether, N-acetyl-4-deoxy-D-neuraminic acid 1 was obtained in an overall yield of about 30% from 2.

引用

页码：181 / 195

页数：15

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