Synthesis and lipophilicity of trifluorinated analogues of glucose.
JOURNAL OF ORGANIC CHEMISTRY(2019)
Abstract
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 C-4(1) 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 F-19 NMR spectroscopy.
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Key words
trifluorinated analogues,glucose,lipophilicity,synthesis
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