Synthetic efforts towards the synthesis of fluorinated C-glycosidic analogues of α-galactosylceramides

International audienceA review of the work realized by the group regarding the synthesis of fluorinated C-glycosides is described. The various strategies that were investigated allowed the synthesis of CF2-glycosides for many carbohydrate series (glucose, mannose and galactose) and for any pseudo-anomeric center configuration (α or β). This work culminated in an efficient prepn. of a synthetically useful α-CF2-galactoside intermediate and its conversion to α-CF2-galactoconjugates. A synthesis of α-CF2-galactosylceramide, based on this last methodol., is currently investigated