Cyclic Sulfur Esters as Substrates for Nucleophilic Substitution. A New Synthesis of 2-Deoxy-2-fluoro-D-glucose

Article abstract of DOI:10.1021/jo00168a026

The 2,3-cyclic sulfites and sulfates of methyl 4,6-O-benzylidene-α- and -β-D-mannopyranoside were synthesized and examined as suitable substrates for the preparation of 2-deoxy-2-fluoro-D-glucose.Both sulfites on reaction with tetramethylammonium fluoride gave reaction products due to attack at sulfur by water.The methyl α-D-glycoside sulfate gave an α,β-unsaturated ketone (7).The β-methyl sulfate reacted cleanly with fluoride and other nucleophiles to give, after hydrolysis, the 2-substituted 2-deoxyglucose compounds.