From Carbohydrates to Complex Organofluorines: Synthesis,Conformation, and Lipophilicity of Multivicinal-Fluorine-Containing Hexitol Analogues |
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Authors: | Danny Lainé Olivier Lessard Jacob St-Gelais Prof Denis Giguère |
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Institution: | Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Quebec City, QC, G1V 0A6 Canada |
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Abstract: | There is growing interest in the preparation of fluorine-containing organic molecules. Multivicinal-fluorine analogues are among the most intriguing and promising compounds, but their physical and biological investigations are held back by challenging syntheses. Herein, we report on the synthesis of a large set of novel polyfluorohexitols. The dominant solution-state conformation of all trifluorohexitols was determined, and the solid-state conformations of some analogues were compared. Finally, the lipophilicity of a large set of polyfluorinated hexopyranose and hexitol analogues was attributed by using a log P determination method based on 19F NMR spectroscopy. |
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Keywords: | fluorinated carbohydrates fluoroalditols lipophilicities solid-state conformations solution-state conformations |
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