Convenient stereoselective synthesis of substituted ureido glycosides using stable 4-chlorophenylcarbamates without the requirement of lewis acids

A modification of the synthesis of substituted ureido glycosides in a stereospecific fashion is described, in which commercially available azido glycosides are reduced to the amines, which are then reacted with 4-chlorophenyl chloroformate to the corresponding 4-chlorophenyl carbamate of the glycosides. These synthetic intermediates are stable at room temperature and have a long shelf life, and can transiently form the 1-isocyanato glycosides under mildly basic conditions, which subsequently can react with amines to form substituted ureido glycosides