FACTORS AFFECTING THE PURITY OF 2-DEOXY-2-FLUORO-D-GLUCOSE SYNTHESIZED FROM THE REACTIONS OF GLYCALS WITH ACETHYL HYPOFLUORITE

Article abstract of DOI:10.1016/S0022-1139(00)81429-3

The reactions of gaseous acethyl hypofluorite with glycals (1a-d) followed by hydrolysis with 2N HCl give 2-deoxy-2-fluoro-D-glucose (2) and 2-deoxy-2-fluoro-D-mannose (3).The ratio of 2 to 3 depends largely on the polarity of the solvent rather than on the size of the substituents on the hydroxyl groups of glucal.The amount of 3 in the final product from the reaction of 1b-d with acethyl hypofluorite ranges from 4percent in non-polar solvents (Freon-11, CCl4, hexane) to ca. 20percent in polar solvents (HOAC, MeOH, DMF, acetone).