Hetero-bifunctionalization of the secondary face of p-cyclodextrin:selective 3~G-sulfonylation and subsequent 2~G,3~G-epoxidation of 3~A-azido-3~A-deoxy-alfr-beta-cyclodextrin

摘要

3~A-Azido-3~A-deoxy-altro-beta-cyclodextrin,which has 20 different hydroxyl groups,was selectively sulfonylated by 1-naph-thalenesulfonyl 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-beta-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.