SYNTHESIS OF TRIFLUOROMETHYL ANALOG OF L-FUCOSE AND 6-DEOXY-D-ALTROSE

Trifluoromethylation of the acyclic derivative of D-lyxose, 3, with trifluoromethyltrimethylsilane in the presence of tetrabutylammonium fluoride yielded a mixture of trifluoromethyl adducts, 5a and b, which was converted to 6,6,6-trifluoro-L-fucose 9a and 6-deoxy-6,6,6-trifluoro-D-altrose 9b via selective oxidation of the primary hydroxy group involving treatment of the trimethylsiloxy derivatives, 7a and b, with Collins reagent.