Issue 7, 1995

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

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1995, 1263-1277

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

P. R. Ashton, E. Y. Hartwell, D. Philp, N. Spencer and J. F. Stoddart, J. Chem. Soc., Perkin Trans. 2, 1995, 1263 DOI: 10.1039/P29950001263

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements