Toggle Main Menu Toggle Search

Open Access padlockePrints

Synthesis of Cyclodextrin-Based Carbohydrate Clusters by Photoaddition Reactions

Lookup NU author(s): Dr David Fulton


Full text for this publication is not currently held within this repository. Alternative links are provided below where available.


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.

Publication metadata

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


DOI: 10.1021/jo010705z


Altmetrics provided by Altmetric