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

In English

Författare

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.

Publiceringsår

2006

Språk

Engelska

Sidor

3444-3451

Publikation/Tidskrift/Serie

Journal of Organic Chemistry

Volym

71

Issue

9

Dokumenttyp

Artikel i tidskrift

Förlag

The American Chemical Society (ACS)

Ämne

  • Medicinal Chemistry

Status

Published

Forskningsgrupp

  • Glycobiology

ISBN/ISSN/Övrigt

  • ISSN: 1520-6904