Selective desulfonylation in D-xylofuranose 3,5-disulfonates

Abstract

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

Keywords

• d-xylofuranose
• sulfonyl ester
• nucleophilic substitution
• desulfonylation