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Regioselective reductive openings of acetals; Mechanistic details and synthesis of fluorescently labeled compounds

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Author

Summary, in English

Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3 center dot NMe3 center dot AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, anti proliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.

Publishing year

2006

Language

English

Pages

3444-3451

Publication/Series

Journal of Organic Chemistry

Volume

71

Issue

9

Document type

Journal article

Publisher

The American Chemical Society (ACS)

Topic

  • Medicinal Chemistry

Status

Published

Research group

  • Glycobiology

ISBN/ISSN/Other

  • ISSN: 1520-6904