Preparation of 2 A,3 A-alloepimino-2 A,3 A-dideoxy-β-cyclodextrin as a versatile scaffold candidate for the hetero-2 A,3 A-bifunctionalization

Abstract

3 A-Azido-3 A-deoxy- altro-β-cyclodextrin, although having as many as 20 different hydroxyl groups, was selectively sulfonylated at the 2 A-OH of the altrose residue by 2-mesitylenesulfonyl chloride to give 3 A-azido-3 A-deoxy-2 A- O-mesitylenesulfonyl- altro-β-cyclodextrin. A one-pot reduction–intramolecular substitution of the latter afforded the title compound as a promising intermediate for the introduction of two different functional groups to two different positions of one sugar unit, which has not been succeeded hitherto.