NEW SYNTHESIS OF 2-DEOXY-2-FLUORO-D-GALACTOSE

Abstract

A nucleophilic displacement reaction of methyl 3, 4-O-isopropylidene-2-O-(trifluoromethanesulfonyl)-6-O-trityl-β-D-talopyranoside (10) with tetraalkylammonium fluorides in acetonitrile gave methyl 2-deoxy-2-fluoro-3, 4-O-isopropylidene-6-O-trityl-β-D-galactopyranoside (11). Excellent conversion of 11 into 2-deoxy-2-fluoro-D-galactose (1) was achieved by hydrolysis with 5 N hydrochloric acid.