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Communication | Special issue | Vol 99, No. 2, 2019, pp.834-840
Published online, 15th January, 2019
DOI: 10.3987/COM-18-S(F)75
α-Glucoside Formation from 2-Deoxy-2-(2,2,2-trichloroethoxycarboxamido)-α-D-glucopyranosyl Acetate Using an Activating System That Used a Combination of Ytterbium(III) Triflate and a Catalytic Boron Trifluoride Diethyl Etherate Complex

Takashi Yamanoi,* Yoshiki Oda, Akihiko Koizumi, Tsubasa Kawaguchi, Shin Yagihara, and Akihiro Yoshida

*Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan


This study describes the formation of α-glucoside from 3,4,6-tri-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarboxamido)-α-D-glucopyranosyl acetate using an activating system that used a combination of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex. This glucoside formation using various types of alcohol acceptors proceeded with high α-stereoselectivity. The novel glucoside method employed in this study is a useful technique for producing 2-amino-2-deoxy-α-D-glucopyranoside derivatives because a 2,2,2-trichloroethoxycarbonyl group from an N-protecting group is easily removable.