Thiocarbonyl as a Switchable Relay-Auxiliary Group in Carbohydrate Synthesis

Abstract

A multifunctional <i>O</i>-phenyl thiocarbonyl (O(C═S)OPh) group was introduced in glycosylation reactions. This auxiliary group exhibits three features (1) <i>C</i>6-long-range participation effect, (2) relay activation, and (3) switchable promoter-controlled carbonylation, which enables the facile synthesis of both 6-deoxy glucoside and 6-alcohol glucoside. In addition, we successfully quantified the extent of the <i>C</i>6-acyl participation effect and developed its application toward the α-trisaccharide motif.