Js. Houlton et al., A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES, Tetrahedron, 49(36), 1993, pp. 8087-8106
A series of carbohydrate gem-difluoroenol ethers are readily prepared
by the reaction of the corresponding lactones with dibromodifluorometh
ane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydro
genation provides difluoromethyl C-glycoside analogues in which the ex
ocyclic oxygen atom has been replaced by a difluoromethylene unit.