Synthesis of 2,6-Dideoxy-6-Thio Derivatives of KDO
作者:
Zhengchun Liu,
Björn Classon,
Per J. Garegg,
Bertil Samuelsson,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1991)
卷期:
Volume 10,
issue 1
页码: 65-76
ISSN:0732-8303
年代: 1991
DOI:10.1080/07328309108543891
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Ammonium 2,3,6-trideoxy-2,6-epithio-D-manno-2-octenoate (8), ammonium 2,3,6-trideoxy-2,6-epithio-D-glycero-D-talo-octanoate (10a), ammonium 2,3,6-trideoxy-2,6-epithio-D-glycero-D-galacto-octanoate (10b) and ammonium 2,3,6-trideoxy-2,6-epithio-oxa-D-glycero-D-galacto-octanoate (13) have been synthesised as potential inhibitors of the enzyme CMP-KDO synthetase. The key step in the synthesis of8was the elimination of water from methyl 3,6-dideoxy-4,5:7,8-di-O-isopropylidene-6-thio-D-manno-2-octulosonate (4) using chlorodiphenylphosphine, imidazole and bromine to give the unsaturated methyl 2,3,6-trideoxy-2,6-epithio-4,5:7,8-di-O-isopropylidene-D-manno-2-octenoate (5). For the synthesis of10aand10b, zinc reduction of methyl 3,6-dideoxy-4,5:7,8-di-O-isopropylidene-6-S-(4-methoxybenzyl)-6-thio-2-O-(trichloro-tert-butoxycarbonyl)-D-manno-2-octenoate (2) gave an epimeric mixture of an α-hydroxyester6which was ring closed by insituactivation of the hydroxyl group using triphenylphosphine and tri-iodoimidazole followed by cleavage of thep-methoxybenzyl group to give7aand7b, which then were deprotected to give10aand10b.
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