The synthesis and structural mapping of unsymmetrical chemically modified α-cyclodextrins by high-field nuclear magnetic resonance spectroscopy

Peter R. Ashton*, Edward Y. Hartwell, Douglas Philp, Neil Spencer, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Hexakis(2,3-di-O-methyl-6-deoxy-6-iodo)-α-cyclodextrin (I-DMαCD) was prepared from hexakis(2,3-di-O-methyl)-αCD (DMαCD) using iodine and triphenylphosphine. The subsequent attempted substitution of I-DMαCD with the phenoxide anions of either 4-hydroxybenzyl alcohol or 4-benzyloxyphenol produced unexpected products. These products were found to be a result of an elimination reaction involving one of the iodomethyl groups to produce one 6-deoxyhex-5-eno-D-glucopyranoside residue within the DMαCD structure in addition to the substitution of the other five iodomethyl groups either by (4-hydroxymethyl)phenyl or by (4-benzyloxy)phenyl ether functions, respectively. The products have been characterised fully using high resolution positive-ion FABMS and high resolution 1H and 13C NMR spectroscopies.

Original languageEnglish (US)
Pages (from-to)1263-1277
Number of pages15
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number7
DOIs
StatePublished - Jan 1 1995

ASJC Scopus subject areas

  • Chemistry(all)

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