Synthesis and spectroscopic characterisation of lipophilic octylated α-, β- and γ-cyclodextrin derivatives

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Abstract
The octylation of α-, β- and γ-cyclodextrin may be undertaken in two steps: reaction with octyl bromide (NaOH–Me2SO) 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 13C NMR analysis of methylated analogues and also by GC–MS analysis of reductively depolymerised samples. Assignment of the 1H and 13C NMR spectra of selected derivatives has been carried out.