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 language | English (US) |
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Pages (from-to) | 1263-1277 |
Number of pages | 15 |
Journal | Journal of the Chemical Society, Perkin Transactions 2 |
Issue number | 7 |
DOIs | |
State | Published - 1995 |
ASJC Scopus subject areas
- General Chemistry