De Novo Enantioselective Synthesis of Hexafluorinated d‑Glucose

We report a de novo enantioselective synthesis of 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro-d-glycero-hexopyranose (hexafluorinated d-glucose), an iconic polar hydrophobic glycomimetic. The 12-step synthesis features robust and reproducible chemistry and was achieved by incorporating an asymmetric dihyd...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-10, Vol.89 (19), p.14291-14304
Main Authors: Depienne, Sébastien, Fontenelle, Clément Q., Light, Mark E., Hecke, Kristof Van, Linclau, Bruno
Format: Article
Language:English
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Summary:We report a de novo enantioselective synthesis of 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro-d-glycero-hexopyranose (hexafluorinated d-glucose), an iconic polar hydrophobic glycomimetic. The 12-step synthesis features robust and reproducible chemistry and was achieved by incorporating an asymmetric dihydroxylation step to install the stereogenic center with excellent enantioselectivity (95:5 er). Virtual enantiopurity (>99.5% ee) was further reached using a simple crystallization procedure and the absolute confirmation was ascertained by X-ray analysis. The synthetic route also allowed access to the novel hexafluorinated heptose derivative 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro-l-threo-heptopyranose.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01724