First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides

The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides.