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 RuO 4 . 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.