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Communication | Regular issue | Vol 94, No. 11, 2017, pp.2031-2037
Published online, 29th September, 2017
DOI: 10.3987/COM-17-13811
1,2-cis-α-Glucoside Formation from a 2-Benzyloxycarbonylamino-2-deoxy-α-D-glucopyranosyl Acetate Derivative by an Activating System That Used a Combination of Ytterbium(Ill) Triflate and a Catalytic Boron Trifluoride Diethyl Etherate Complex

Takashi Yamanoi,* Yoshiki Oda, Kento Fujita, and Akihiko Koizumi

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


We investigated a glucoside formation reaction that utilized a 2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranosyl acetate donor derivative and various types of alcohol acceptors. The reaction was promoted by an activating system that used a combination of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex, and it gave the corresponding 1,2-cis-α-glucopyranosides with high stereoselectivity. This glucoside reaction is a new and useful method for producing α-glucopyranoside derivatives from 2-amino-2-deoxy-D-glucopyranose.