Cyclic sulfates containing acid-sensitive groups and chemoselective hydrolysis of sulfate esters

Abstract

Diols containing acid-sensitive functionalities such as acetonide and silyloxy groups are efficiently converted to the corresponding cyclic sulfates via formation of the cyclic sulfites in the presence of a base and oxidation of the isolated sulfites using catalytic RuO4. Reactions of these cyclic sulfates with nucleophiles such as azide and benzoate provide sulfates, which can be successfully hydrolyzed by using a catalytic amount of sulfuric acid and 0.5∼1.0 eq of water in THF.