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Communication | Special issue | Vol 88, No. 1, 2014, pp.201-206
Published online, 7th August, 2013
DOI: 10.3987/COM-13-S(S)44
Formation of 1,2-cis-α-Aryl-glycosidic Linkages Directly from 2-Acetamido-2-deoxy-D-glucopyranosyl Acetate by the Mixed Activating System Using Ytterbium(III) Triflate and Catalytic Boron Trifluoride Diethyl Etherate Complex

Takashi Yamanoi,* Masanobu Midorikawa, and Yoshiki Oda

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

Abstract

We found that a mixed activating system using ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promoted glycosidation of the 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 along with the formation of a considerable amount of α-isomers. Glycosylations of the aryl alcohols as the acceptors stereoselectively afforded aryl α-glycosides without producing any β-isomers.