Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose.

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 4 C1 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.