The Allyl Group for Protection in Carbohydrate Chemistry, Part 14.1Synthesis of 2, 3-Di-O-Methyl-4-O-(3, 6-Di-O-Methyl-β-D-Glucopyranosyl)-L-Rhamnopyranose (and its α-Propyl Glycoside): A Haptenic Portion of the Major Glycolipid fromMycobacterium Leprae
作者:
Roy Gigg,
Sheila Payne,
Robert Conant,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1983)
卷期:
Volume 2,
issue 3
页码: 207-223
ISSN:0732-8303
年代: 1983
DOI:10.1080/07328308308057870
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
3, 6-Di-O-methyl-d-glucose was preparedvia5-O-allyl-1, 2-O-isopropylidene-3-O-methyl-αd-glucofuranose and was converted into 2, 4-di-O-acetyl-3, 6-di-o-methyl-dD-glucopyranosy 1 chloride. Condensation of the chlorosugar with methanol or allyl 2, 3-O-isopropylidene-α-l-rhamnopyranoside gave the corresponding crystalline β-glycbsides. The allyl 4-O-(2,4-di-O-acetyl-3, 6-di-O-Tnethyl-β-dD-glucopyranosyl)-2, 3-O-isopropylidene-α-l-rhamnopyranoside was converted into the title compounds and into crystalline 2, 3-di-O-acetyl-4-O-(2, 4-di-O-benzyl-3, 6-di-O-methyl-β-d-glucopyranosyl)-l-rhamnopyranosyl chloride which should serve as an intermediate for the synthesis of the trisaccharide portion of the major glycolipid ofMycobacterium leprae.
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