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- Publisher Website: 10.1021/jo010705z
- Scopus: eid_2-s2.0-0035861618
- PMID: 11735508
- WOS: WOS:000172606000005
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Article: Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions
Title | Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions |
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Authors | |
Issue Date | 2001 |
Citation | Journal of Organic Chemistry, 2001, v. 66, n. 25, p. 8309-8319 How to Cite? |
Abstract | The syntheses of homogeneous cyclodextrin-based carbohydrate clusters, persubstituted with β-D-thioglucosyl or D-thiolactosyl residues on either (a) the primary face, (b) the secondary face, or (c) both the primary and the secondary faces of their cyclodextrin tori, are described. The key step in the synthetic methodology, namely the attachment of the carbohydrate residues to the cyclodextrin torus, proceeds in moderate-good yields (42-70%) by the photoaddition of thiol groups, positioned at the anomeric centers of the carbohydrate residues, to allyl ether functions on the cyclodextrins. Facile removal of protecting groups then affords the free cluster compounds. Extensive 1-D and 2-D NMR spectroscopic investigations were performed on these compounds to determine their structures and establish their homogeneities, and a brief computer molecular modeling study allowed estimates of the dimensions of the clusters to be determined. |
Persistent Identifier | http://hdl.handle.net/10722/332495 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Fulton, D. A. | - |
dc.contributor.author | Stoddart, J. F. | - |
dc.date.accessioned | 2023-10-06T05:11:57Z | - |
dc.date.available | 2023-10-06T05:11:57Z | - |
dc.date.issued | 2001 | - |
dc.identifier.citation | Journal of Organic Chemistry, 2001, v. 66, n. 25, p. 8309-8319 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332495 | - |
dc.description.abstract | The syntheses of homogeneous cyclodextrin-based carbohydrate clusters, persubstituted with β-D-thioglucosyl or D-thiolactosyl residues on either (a) the primary face, (b) the secondary face, or (c) both the primary and the secondary faces of their cyclodextrin tori, are described. The key step in the synthetic methodology, namely the attachment of the carbohydrate residues to the cyclodextrin torus, proceeds in moderate-good yields (42-70%) by the photoaddition of thiol groups, positioned at the anomeric centers of the carbohydrate residues, to allyl ether functions on the cyclodextrins. Facile removal of protecting groups then affords the free cluster compounds. Extensive 1-D and 2-D NMR spectroscopic investigations were performed on these compounds to determine their structures and establish their homogeneities, and a brief computer molecular modeling study allowed estimates of the dimensions of the clusters to be determined. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of Organic Chemistry | - |
dc.title | Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jo010705z | - |
dc.identifier.pmid | 11735508 | - |
dc.identifier.scopus | eid_2-s2.0-0035861618 | - |
dc.identifier.volume | 66 | - |
dc.identifier.issue | 25 | - |
dc.identifier.spage | 8309 | - |
dc.identifier.epage | 8319 | - |
dc.identifier.isi | WOS:000172606000005 | - |