Stereocontrolled Formation ofProtected Aminodeoxyalditols from Simple Carbohydrate Precursorsby Debenzylating Cycloetherification

Abstract

A new and highly efficient methodology for the stereocontrolled synthesis of aminodeoxyalditols is described through a dimesylation/intramolecular SN2 nucleophilic substitution ring-forming reaction sequence from glucose, mannose, and galactose derivatives. The degree of difficulty and rate of the reaction of dimesylates in the cyclization process is evaluated and shows the trend: galactose > glucose > mannose derivatives, which has been identified from our experiments and classical theories.