Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 6, Issue 7, Pages 1876-1885Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201000896
Keywords
glycosides; glycosylation; mercaptopyridine; oligosaccharides; protecting groups
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Funding
- Ministry of Education, Sports, Science and Technology
- NEDO of Japan
- International Center of Research & Education for Molecular Complex Chemistry from Tohoku University
- Grants-in-Aid for Scientific Research [22550105, 20350051, 22850010, 21750109, 23655094] Funding Source: KAKEN
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Various 2-pyridyl 1-thioglycosides, important synthetic intermediates and enzyme inhibitors in sugar chemistry, have been synthesized directly from the corresponding unprotected sugars in good yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as dehydrative condensing agent. The reaction proceeds in aqueous media without using any protecting groups, affording 2-pyridyl 1-thioglycosides with beta-configuration selectively. According to the present method, not only unprotected monosaccharides but also unprotected oligosaccharides, such as cello-oligosaccharides, chito-oligosaccharides, malto-oligosaccharides, and glucosamine oligomers, can be converted to the corresponding 2-pyridylthio derivatives, which would greatly expand the utility of aryl 1-thioglycosides in sugar chemistry.
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