A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives

Article abstract of DOI:10.1016/S0040-4020(98)00189-6

A new type of reactive N-(2-deoxy-2-fluoro-glycosyl) compound is formed by regioselective syn-addition of the electrophilic N-F reagent Selectfluor(TM) to glycals. By subsequent treatment with nucleophiles, 2- deoxy-2-fluoro-aldoses and various C-1-substituted derivatives thereof are easily accessible. Furthermore, the reaction with D-galactal and D-arabinal proceeds stereoselectively, thus allowing the synthesis of 2-deoxy-2-fluoro- D-galactose- and -D-arabinose-derivatives in multi-gram quantities.