Stereoselective synthesis of glycosyl azides from anomeric hydroxides via protecting group manipulations.

ABSTRACT

Herein, we report the direct conversion of anomeric hydroxides to glycosyl azides in one step using diphenylphosphoryl azide. Protecting group manipulations on the hexose sugars have enabled the stereoselective synthesis of either the α-glycosyl azides or the ß-anomeric azides in moderate to very good yields. The reaction has also been successfully used to enable the synthesis of ß-2-deoxy-2-aminoglucosyl azides.