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Article: The synthesis and structural mapping of unsymmetrical chemically modified α-cyclodextrins by high-field nuclear magnetic resonance spectroscopy
Title | The synthesis and structural mapping of unsymmetrical chemically modified α-cyclodextrins by high-field nuclear magnetic resonance spectroscopy |
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Authors | |
Issue Date | 1995 |
Citation | Journal of the Chemical Society, Perkin Transactions 2, 1995, n. 7, p. 1263-1277 How to Cite? |
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. |
Persistent Identifier | http://hdl.handle.net/10722/332757 |
ISSN | |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Ashton, Peter R. | - |
dc.contributor.author | Hartwell, Edward Y. | - |
dc.contributor.author | Philp, Douglas | - |
dc.contributor.author | Spencer, Neil | - |
dc.contributor.author | Fraser Stoddart, J. | - |
dc.date.accessioned | 2023-10-06T05:14:02Z | - |
dc.date.available | 2023-10-06T05:14:02Z | - |
dc.date.issued | 1995 | - |
dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 2, 1995, n. 7, p. 1263-1277 | - |
dc.identifier.issn | 1472-779X | - |
dc.identifier.uri | http://hdl.handle.net/10722/332757 | - |
dc.description.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. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the Chemical Society, Perkin Transactions 2 | - |
dc.title | The synthesis and structural mapping of unsymmetrical chemically modified α-cyclodextrins by high-field nuclear magnetic resonance spectroscopy | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/p29950001263 | - |
dc.identifier.scopus | eid_2-s2.0-37049070462 | - |
dc.identifier.issue | 7 | - |
dc.identifier.spage | 1263 | - |
dc.identifier.epage | 1277 | - |
dc.identifier.isi | WOS:A1995RJ36900004 | - |