Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions

D. A. Fulton, J. F. Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)8309-8319
Number of pages11
JournalJournal of Organic Chemistry
Volume66
Issue number25
DOIs
StatePublished - Dec 14 2001

ASJC Scopus subject areas

  • Organic Chemistry

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