Synthesis and transformations of d-glucuronic and l-iduronic acid glycals

Abstract

d-Glucuronic acid glycals can be efficiently synthesized from diacetone glucose or tri- O-acetyl glycal and can be transformed into d-glucuronic acid donors and acceptors in high yields. Base catalyzed epimerization of d-glucuronic acid glycals provides access to the corresponding l-iduronic acid glycals. Both d-glucuronic and l-iduronic acid glycals were transformed into glycosylating agents for use in the synthesis of glycosaminoglycan oligosaccharides.