β-Selective glucosylation in the absence of neighboring group participation: influence of the 3,4-O-bisacetal protecting system

A 3,4-O-bisacetal 2,6-di-O-benzyl protected thioglucoside is converted to the corresponding glucosyl triflate with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. The moderate to excellent β-selectivity exhibited with this glucosyl triflate with a range of alcohols is generally higher than that observed with the more electronically disarmed corresponding 3,4-O-carbonate, for which a possible reason is advanced.