Regioselective 2A,2D-disulfonyl capping of β-cyclodextrin for practical bifunctionalization on the secondary hydroxyl face

A useful technique to bifunctionalize the secondary hydroxyl face of β-cyclodextrin is described. Regioselective 2A,2D-disulfonylation of β-cyclodextrin was achieved by reacting β-cyclodextrin with a combination of a novel disulfonyl imidazole reagent and molecular sieves in DMF. The resulting disulfonate was converted to 2A,3A,2D,3D-dimannoepoxy-β-cyclodextrin and 3A,3D-diamino-3A,3D-dideoxy-(2AS,3AS),(2DS,3DS)-β-cyclodextrin, which contains two functional groups on the periphery of the molecule.