The rapid synthesis of deoxyfluoro sugars using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)

Abstract

Deoxyfluoro sugars were synthesized rapidly by the reaction of trifluoromethanesulfonyl derivatives of partially protected sugars with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) under mild conditions. The displacements occurred with inversion of configuration; fluorine has been introduced stereospecifically at each of the secondary alcoholic sites of aldohexopyranosides and in one example of a furanoid system. In some instances unsaturated compounds that contained no fluorine were produced.