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A Chiron approach towards the stereoselective synthesis of polyfluorinated carbohydrates

Author

Listed:
  • Vincent Denavit

    (Université Laval PROTEO, RQRM)

  • Danny Lainé

    (Université Laval PROTEO, RQRM)

  • Jacob St-Gelais

    (Université Laval PROTEO, RQRM)

  • Paul A. Johnson

    (Université Laval PROTEO, RQRM)

  • Denis Giguère

    (Université Laval PROTEO, RQRM)

Abstract

The replacement of hydroxyl groups by fluorine atoms on hexopyranose scaffolds may allow access to the discovery of new chemical entities possessing unique physical, chemical and ultimately even biological properties. The prospect of significant effects generated by such multiple and controlled substitutions encouraged us to develop diverse synthetic routes towards the stereoselective synthesis of polyfluorinated hexopyranoses, six of which are unprecedented. Hence, we report the synthesis of heavily fluorinated galactose, glucose, mannose, talose, allose, fucose, and galacturonic acid methyl ester using a Chiron approach from inexpensive levoglucosan. Structural analysis of single-crystal X-ray diffractions and NMR studies confirm the conservation of favored 4C1 conformation for fluorinated carbohydrate analogs, while a slightly distorted conformation due to repulsive 1,3-diaxial F···F interaction is observed for the trifluorinated talose derivative. Finally, the relative stereochemistry of multi-vicinal fluorine atoms has a strong effect on the lipophilicities (logP).

Suggested Citation

  • Vincent Denavit & Danny Lainé & Jacob St-Gelais & Paul A. Johnson & Denis Giguère, 2018. "A Chiron approach towards the stereoselective synthesis of polyfluorinated carbohydrates," Nature Communications, Nature, vol. 9(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-06901-y
    DOI: 10.1038/s41467-018-06901-y
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