Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 12. A study of cyclic iminocarbonates

Abstract

A novel method for the replacement of a carbohydrate hydroxy-group by an amino-function via rearrangement of cyclic iminocarbonates has been developed. Several examples from the carbohydrate field illustrate that the overall process is strongly influenced both by the nature of the substituent attached to the nitrogen atom of the iminocarbonate ring, and by stereoelectronic factors inherent in the substrate structure.