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 C 2 , C 3 , or C 6 atoms in the carbohydrate fragments on the basis of 13 C 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.

Mono-6-Substituted Cyclodextrins—Synthesis and Applications

“…Edunov et al [ 95 ] have utilized TEA as a nucleophilic catalyst and a base instead of pyridine or DMAP in their work about selectively substituted CDs. The authors performed benzoylation of α-CD in DMF.…”