Synthesis Of 2-Acetamido-2-Deoxy-5-Thio-α-D-Galactopyranose
作者:
Eiji Tanahashi,
Makoto Kiso,
Akira Hasegawa,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1983)
卷期:
Volume 2,
issue 2
页码: 129-137
ISSN:0732-8303
年代: 1983
DOI:10.1080/07328308308057862
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
When treated with a large excess of 2,2-dimethoxypropane in the presence ofp-toluenesulfonic acid in 1,4-dioxane, 2-acetamido-2-deoxy-D-galactose gave methyl 2-acetamido-2-deoxy-5,6-0-iso-propylidene-α- and -β-D-galactofuranosides, which were converted,viabenzoylation andO-deisopropylidenation, into methyl 2-acetami-do-3-O-benzoyl-2-deoxy-α- and -β-D-galactofuranosides (3,4). Selective benzoylation of 4, followed by mesylation, gave methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-5-O-mesyl-β-D-galactofurano-side (6), which was treated with sodium methoxide to give the 5,6-anhydro derivative (7). Treatment of7with thiourea, followed by cleavage of the epithio ring in8, afforded the 5-thio compound9. Alkaline treatment of10, derived from9by hydrolysis, yielded the title compound.
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