alpha-GLUCOSIDE FORMATION FROM 2-DEOXY-2-(2,2,2-TRICHLOROETHOXYCARBOXAMIDO)-alpha-D-GLUCOPYRANOSYL ACETATE USING AN ACTIVATING SYSTEM THAT USED A COMBINATION OF YTTERBIUM(III) TRIFLATE AND A CATALYTIC BORON TRIFLUORIDE DIETHYL ETHERATE COMPLEX

This study describes the formation of a-glucoside from 3,4,6-tri-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarboxamido)-alpha-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 alpha-stereoselectivity. The novel glucoside method employed in this study is a useful technique for producing 2-amino-2-deoxy-alpha-D-glucopyranoside derivatives because a 2,2,2-trichloroethoxycarbonyl group from an N-protecting group is easily removable.