Abstract
3 A-Azido-3 A-deoxy- altro-β-cyclodextrin, which has 20 different hydroxyl groups, was selectively sulfonylated by 1-naphthalenesulfonyl chloride at the 3 G-OH of the glucoside residue as well as the 2 A-OH of the altroside one. Alkali treatment of the 3 G-sulfonate gave successfully the 2 G,3 G-epoxyalloside with the 3 A-azido group being left unaffected. Both the 3 G-sulfonate and 2 G,3 G -alloepoxide species of 3 A-azido-3 A-deoxy- altro-β-cyclodextrin not only have two sugar units being modified differently, but also can serve as versatile starting materials for the syntheses of bifunctional cyclodextrins with diverse combination of different functionalities.
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