Specific Preparation and Structure Determination of 3A,3C,3E-Tri-O-sulfonyl-β-cyclodextrin

Article abstract of DOI:10.1021/jo00290a016

A reaction of β-cyclodextrin with β-naphthylsulfonyl chloride in alkaline aqueous acetonitrile gave only one isomer (3^A,3^C,3^E-trisulfonate, 17.8percent) of five 3,3,3-tri-O-sulfonyl-β-cyclodextrins.The isomer was converted to 3^A,6^A:3^C,6^C:3^E,6^E-trianhydro-β-cyclodextrin, the structure of which was assigned by comparing its spectral and HPLC data of the trianhydro-β-cyclodextrin with those of all authentic 3,6:3,6:3,6-trianhydro-β-cyclodextrins prepared by the reactions of known 6-tri-O-sulfonylated β-cyclodextrins with aqueous alkali.