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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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