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Paper | Special issue | Vol 99, No. 1, 2019, pp.350-362
Published online, 19th October, 2018
DOI: 10.3987/COM-18-S(F)28
Arylboronic Acid-Mediated Glycosylation of 1,2-Dihydroxyglucoses

Sanae Izumi, Yusuke Kobayashi, and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

We explored direct dehydrative coupling of tetrahydro-2H-pyran-2,3-diol or a 1,2-dihydroxy sugar with various alcohols using a range of arylboronic acids. Among the catalysts, 2-borono-4-trifluoromethylbenzoic acid efficiently promoted acetalization of tetrahydro-2H-pyran-2,3-diol. Ferroceniumboronic acid showed the best catalytic activity for glycosylation of the 1,2-dihydroxy sugar. The major products were 1,2-cis-α-D-glucopyranosides.