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

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Abstract

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.

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Subject classification (UKÄ) – MANDATORY

  • Medicinal Chemistry
Original languageEnglish
Pages (from-to)3444-3451
JournalJournal of Organic Chemistry
Volume71
Issue number9
Publication statusPublished - 2006
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Glycobiology (013212006)