Abstract
A useful technique to bifunctionalize the secondary hydroxyl face of β-cyclodextrin is described. Regioselective 2 A,2 D-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 2 A,3 A,2 D,3 D-dimannoepoxy-β-cyclodextrin and 3 A,3 D-diamino-3 A,3 D-dideoxy-(2 A S,3 A S),(2 D S,3 D S)-β-cyclodextrin, which contains two functional groups on the periphery of the molecule.
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