title: Direct dehydrative pyridylthio-glycosidation of unprotected sugars in aqueous media using 2-chloro-1,3-dimethylimidazolinium chloride as a condensing agent.
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.
authors: Graduate School of Engineering, Tohoku University, 6-6-11-513, Aramaki, Aoba, Sendai, Miyagi 980-8579, Japan.
authors: Naoki
authors: N
authors: Yoshida
authors: Masato
authors: M
authors: Noguchi
authors: Tomonari
authors: T
authors: Tanaka
authors: Takeshi
authors: T
authors: Matsumoto
authors: Naoya
authors: N
authors: Aida
authors: Masaki
authors: M
authors: Ishihara
authors: Atsushi
authors: A
authors: Kobayashi
authors: Shin-ichiro
authors: S
authors: Shoda