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Communication | Regular issue | Vol 68, No. 4, 2006, pp.673-677
Published online, 7th March, 2006
DOI: 10.3987/COM-06-10684
The Brφnsted Acid-catalyzed O-Glycosidation of 1-C-Alkyl-D-glucopyranose Derivatives

Takashi Yamanoi,* Sho Matsuda, Ippo Yamazaki, Ryo Inoue, Keita Hamasaki, and Mikio Watanabe

*The Noguchi Institute, 1-8-1, Kaga, Itabashi-ku, Tokyo 173-0003, Japan

Abstract

We found that the O-glycosidation between various kinds of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses and alcohols in the presence of 5 mol % of trifluoromethanesulfonic acid or bis(trifluoromethane)sulfonimide stereoselectively produced the corresponding 1-C-alkyl-α-D-glucopyranosides in good yields.