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.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA.
Subramanian
Venkataraman
V
Hutton
Thomas K
TK
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