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Direct Dehydrative Pyridylthio‐Glycosidation of Unprotected Sugars in Aqueous Media Using 2‐Chloro‐1,3‐dimethylimidazolinium Chloride as a Condensing Agent
Author(s) -
Yoshida Naoki,
Noguchi Masato,
Tanaka Tomonari,
Matsumoto Takeshi,
Aida Naoya,
Ishihara Masaki,
Kobayashi Atsushi,
Shoda Shinichiro
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000896
Subject(s) - chemistry , monosaccharide , aqueous solution , chloride , sugar , organic chemistry , aryl , aqueous medium , glucosamine , combinatorial chemistry , alkyl
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 β‐configuration selectively. According to the present method, not only unprotected monosaccharides but also unprotected oligosaccharides, such as cello‐oligosaccharides, chito‐oligo‐saccharides, 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.