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From Carbohydrates to Complex Organofluorines: Synthesis, Conformation, and Lipophilicity of Multivicinal‐Fluorine‐Containing Hexitol Analogues
Author(s) -
Lainé Danny,
Lessard Olivier,
StGelais Jacob,
Giguère Denis
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004646
Subject(s) - lipophilicity , fluorine , chemistry , molecule , nuclear magnetic resonance spectroscopy , stereochemistry , solid state , organic chemistry , computational chemistry , combinatorial chemistry
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 19 F NMR spectroscopy.