REACTION OF ACETYL HYPOFLUORITE WITH PYRANOID AND FURANOID GLYCALS

Article abstract of DOI:10.1016/0008-6215(87)80196-9

The regiospecific syn-addition of acetyl hypofluorite to glycals derived from pentopyranoses led to mixtures of stereoisomers.Stereospecific reactions occured with furanoid glycals, the direction of addition being governed by the nature of the substituent at C-3.Whereas a benzyloxy group caused attack from the opposite, less-hindered face of the double bond, a hydroxyl group induced addition from the same side.From these reactions, 2-deoxy-2-fluoro derivatives of β-D-arabino-, α-D-ribo-, β-D-lyxo-, and α-D-xylo-pyranose as well as β-D-manno-, α-D-guco-, α-D-ribo-, and β-D-arabino-furanose were obtained; their 1H-, 13C-, and 19F-n.m.r. data are given.