Asymmetric synthesis of fluorocarbohydrates

We are pursuing an approach of asymmetricsynthesis of fluorinated analogues of biologically active compounds. The framework of chiral carbon atoms of the target molecule is built up around a chiral fluorinated synthon, of synthetic origin, in which an optically pure sulphinyl residue works as a chiral auxiliary agent. The transformation of the (2S,3R)-3-fluoro-1[(R)-(4-methylphenyl)sulphinyl]-5-hexen-2-ol (1), obtained starting from (R)-methyl 4-methylphenyl sulphoxide, ethyl fluoroacetate, and allyl bromide, into the 2,3-dideoxy-3-fluoro-D-erythro-pentose (2) and into the 3,4-dideoxy-3-fluoro-D-arabino-hexose (3) will be described. The synthesis of other monofluoro-pentoses and hexoses will be described and we will report also the preparation of some nitrogen-containing compounds