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Paper | Special issue | Vol 90, No. 1, 2015, pp.198-215
Published online, 26th March, 2014
DOI: 10.3987/COM-14-S(K)4
■ Formation of 2-Acetamido-2-deoxy-D-glucopyranosidic Linkages via Glycosidation Using a Combination of Two Lewis Acids

Yoshiki Oda, Masanobu Midorikawa, and Takashi Yamanoi*

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

Abstract

A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields with significant formation of the α-isomers. Notably, stereoselective glycosylations of phenol derivatives as the acceptors afforded aryl 1,2-cis-α-glycosides without the formation of any β-isomers. This highly stereocontrolled 1,2-cis-α-glycosidation was applied to the synthesis of a novel hydroquinone α-glycoside.