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

Paul S. Bates, David Parker, Antonio F. Patti

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24 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)657-668
Number of pages12
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number4
Publication statusPublished - 1 Jan 1994

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