1,2-cis-alpha-GLUCOSIDE FORMATION FROM A 2-BENZYLOXY-CARBONYLAMINO-2-DEOXY-alpha-D-GLUCOPYRANOSYL ACETATE DERIVATIVE BY AN ACTIVATING SYSTEM THAT USED A COMBINATION OF YTTERBIUM(III) TRIFLATE AND A CATALYTIC BORON TRIFLUORIDE DIETHYL ETHERATE COMPLEX

摘要

We investigated a glucoside formation reaction that utilized a 2-benzyloxycarbonylamino-2-deoxy-alpha-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-alpha-glucopyranosides with high stereoselectivity. This glucoside reaction is a new and useful method for producing alpha-glucopyranoside derivatives from 2-amino-2-deoxy-D-glucopyranose.