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

Herein, we report the direct conversion of anomeric hydroxides to glycosyl azides in one step using diphenyl-phosphoryl azide. Protecting group manipulations on the hexose sugars have enabled the stereoselective syn-thesis of either the alpha-glycosyl azides or the 8-anomeric azides in moderate to very good yields. The reaction has also been successfully used to enable the synthesis of 8-2-deoxy-2-aminoglucosyl azides.

Automated summary

We report a direct method for converting anomeric hydroxides to glycosyl azides using diphenyl-phosphoryl azide. Protecting group manipulations on the hexose sugars allowed for the stereoselective synthesis of either alpha-glycosyl azides or 8-anomeric azides in moderate to very good yields. The reaction was also successfully used for the synthesis of 8-2-deoxy-2-aminoglucosyl azides.