A New Synthesis ofN-Acetyl-4-Deoxy-D-Neuraminic Acid
作者:
Geneviève Estenne,
Alfred Saroli,
Alain Doutheau,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1991)
卷期:
Volume 10,
issue 2
页码: 181-195
ISSN:0732-8303
年代: 1991
DOI:10.1080/07328309108543900
出版商: Taylor & Francis Group
数据来源: Taylor
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-1-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). AfterO-deacetylation, saponification of the ester group and simultaneous deprotection of the silyloxy enol ether,N-acetyl-4-deoxy-D-neuraminic acid1was obtained in an overall yield of about 30% from 2.
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