Selective desulfonylation in D-xylofuranose 3,5-disulfonates

Abstract

A method for the preparation of D-xylofuranosc derivatives with a free terminal (C5) alcohol function was developed, starting from monocyclohexylidcnc-3,5-disulfonyl-or 5-O-sulfonyl-3-O-methyl ester. The regioselective displacement of the C5 sulfonyl ester function with acetate ion in dimethylsulfoxide afforded the corresponding 5-O-acetyl-1,2-O-cyclohexylidene-3-O-sulfonyl or 5-O-acetyl-3-O-methyl-α-D-xylofuranose. These esters could be readily hydrolyscd into the desired 1,2,3-trisubstituted xylofuranose.