Stereospecific synthesis of aldoses based on the epoxide-opening reaction with double inversion of the configuration

A new synthetic methodology for aldoses and aldonitols was developed in which two stereospecific epoxide-opening reactions with double inversion of the configuration, i.e., the ring-opening reaction of epoxy sulfides with phenylboronic acid and the stereospecific interconversion of trans- and cis-epoxy sulfides, were designed as the key steps. The synthetic potential of the new methodology was exemplified by the highly stereoselective synthesis of two pentose-derived sugars, arabitol and adonitol (ribitol).