SYNTHESIS AND SPECTROSCOPIC CHARACTERIZATION OF LIPOPHILIC OCTYLATED ALPHA-CYCLODEXTRIN, BETA-CYCLODEXTRIN AND GAMMA-CYCLODEXTRIN DERIVATIVES

The octylation of alpha-, beta- and gamma-cyclodextrin may be undertaken in two steps: reaction with octyl bromide (NaOH-Me(2)SO) gives relatively monodisperse 2,6-di-O-alkylated material and further reaction (NaH-THF) with octyl bromide yields incompletely octylated products. Complete alkylation may be achieved with KH-18-crown-6-THF. Quantification of the degree of octylation was achieved directly by electrospray mass spectrometry and C-13 NMR analysis of methylated analogues and also by GC-MS analysis of reductively depolymerised samples. Assignment of the H-1 and C-13 NMR spectra of selected derivatives has been carried out.