Direct dehydrative pyridylthio-glycosidation of unprotected sugars in aqueous media using 2-chloro-1,3-dimethylimidazolinium chloride as a condensing agent

Naoki Yoshida, Masato Noguchi, Tomonari Tanaka, Takeshi Matsumoto, Naoya Aida, Masaki Ishihara, Atsushi Kobayashi, Shinichiro Shoda

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1876-1885
Number of pages10
JournalChemistry - An Asian Journal
Volume6
Issue number7
DOIs
Publication statusPublished - 2011 Jul 4

Keywords

  • glycosides
  • glycosylation
  • mercaptopyridine
  • oligosaccharides
  • protecting groups

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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