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Lookup NU author(s): Professor David Fulton
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The syntheses of homogeneous cyclodextrin-based carbohydrate clusters, persubstituted with beta -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.
Author(s): Fulton DA, Stoddart JF
Publication type: Article
Publication status: Published
Journal: The Journal Of Organic Chemistry
Year: 2001
Volume: 66
Issue: 25
Pages: 8309-8319
ISSN (print): 0022-3263
ISSN (electronic): 1520-6904
Publisher: American Chemical Society
URL: http://dx.doi.org/10.1021/jo010705z
DOI: 10.1021/jo010705z
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