Chemical Modification of Maltose. VI. Selective p-Toluenesulfonylation of 1, 6-Anhydro-4', 6'-O-benzylidene-β-maltose using Phase Transfer Catalysis

Abstract

Treatment of 1, 6-anhydro-4', 6'-O-benzylidene-β-maltose (1) in dichloromethane with 1.2 eq of tosyl chloride in the presence of tetrabutylammonium hydrogen sulfate and 4% sodium hydroxide gave the corresponding 2'-O-tosylate (5) as the main product (64.2%). Compound 5 is a versatile intermediate for the chemical modification of maltose.