
Journal of Organic Chemistry p. 8509 - 8522 (2019)
Update date:2022-08-17
Topics:
St-Gelais, Jacob
Bouchard, Megan
Denavit, Vincent
Giguère, Denis
In this work, we have developed synthetic routes for novel trifluorinated glucopyranose analogues using a Chiron approach. This strategy used inexpensive levoglucosan as a starting material, and we achieved a microwave glycosylation method as a key step. All analogues adopted standard 4C1 glucopyranose conformations, and a gauche-gauche conformation for the fluoromethyl group (C5-C6 linkage) was ascertained for congeners with a fluorine atom at C-6. Finally, the lipophilicity of trifluorinated glucose analogues was assessed with a log P determination method based on 19F NMR spectroscopy.
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