α-Cyclodextrin compounds containing benzoic, acetylsalicylic, and 2-(4-isobutylphenyl)propionic acid residues

Abstract

Selectively substituted derivatives of α-cyclodextrin and hexa-O-tert-butyldimethylsilyl-α-cyclodextrin containing a definite number of acylated primary or secondary hydroxy groups were synthesized using benzoic, acetylsalicylic, and 2-(4-isobutylphenyl)propionic acid chlorides in various solvents in the presence of different bases. The acyl residues were assigned to the C2, C3, or C6 atoms in the carbohydrate fragments on the basis of 13C NMR data. Desilylation of the silyl derivatives with ammonium fluoride in methanol gave the corresponding O-acyl derivatives having free primary hydroxy groups in the α-cyclodextrin skeleton.