Specific preparation and structure determination of 3A,3C,3E-tri-O-sulfonyl-.beta.-cyclodextrin

A reaction of β-cyclodextrin with β-naphthylsulfonyl chloride in alkaline aqueous acetonitrile gave only one isomer (3 A ,3 C ,3 E -trisulfonate, 17.8%) 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