Cyclic sulfates in the regioselective synthesis of 5- and 6-amino and 5- and 6-fluorohexofuranoses

Cyclic sulfates of 5,6- and 3,5-d-glucofuranose were used to prepare 6- and 5-azido (amino) and 6- and 5-fluoro derivatives of 1,2-O-isopropylidenehexofuranoses (d-gluco and l-ido configurations). The reactions were completely regioselective and, in the case of stereogenic centers (substitution at C-5), completely stereoselective.