Regioselective reductive openings of acetals; mechanistic details and synthesis of fluorescently labeled compounds.
Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3.NMe3-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, antiproliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.
Johnsson
Richard
R
Organic Chemistry, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
Mani
Katrin
K
Cheng
Fang
F
Ellervik
Ulf
U
D016475:3T3 Cells; D000080:Acetals / Q000737:chemistry*; D000818:Animals; D049109:Cell Proliferation / Q000187:drug effects; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D010084:Oxidation-Reduction
D000080:Acetals; D005456:Fluorescent Dyes; D006027:Glycosides; C010807:xylosides