TY - JOUR
T1 - Direct dehydrative pyridylthio-glycosidation of unprotected sugars in aqueous media using 2-chloro-1,3-dimethylimidazolinium chloride as a condensing agent
AU - Yoshida, Naoki
AU - Noguchi, Masato
AU - Tanaka, Tomonari
AU - Matsumoto, Takeshi
AU - Aida, Naoya
AU - Ishihara, Masaki
AU - Kobayashi, Atsushi
AU - Shoda, Shin Ichiro
PY - 2011/7/4
Y1 - 2011/7/4
N2 - 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.
AB - 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.
KW - glycosides
KW - glycosylation
KW - mercaptopyridine
KW - oligosaccharides
KW - protecting groups
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U2 - 10.1002/asia.201000896
DO - 10.1002/asia.201000896
M3 - Article
C2 - 21604376
AN - SCOPUS:79959994468
VL - 6
SP - 1876
EP - 1885
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 7
ER -