De Novo enantioselective synthesis of hexafluorinated d-glucose
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-Dglycero-
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 crystallisation procedure and the absolute confirmation was ascertained by X-ray analysis. The synthetic route also allowed the access to the novel hexafluorinated heptose derivative 2,3,4-trideoxy-2,2,3,3,4,4- hexafluoro-L-threo-heptopyranose.
14291-14304
Depienne, Sébastien
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Fontenelle, Clement Q
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Light, Mark
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Van Hecke, Kristof
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Linclau, Bruno
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Depienne, Sébastien
cd74a8fb-7597-4ba6-aa4e-e6ec4ccf5bc6
Fontenelle, Clement Q
c746c5ea-96bc-46c2-849d-47215ab58c03
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Van Hecke, Kristof
d5bd05d7-ecd5-41a3-a895-ac9580bc43ce
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Depienne, Sébastien, Fontenelle, Clement Q, Light, Mark, Van Hecke, Kristof and Linclau, Bruno
(2024)
De Novo enantioselective synthesis of hexafluorinated d-glucose.
Journal of Organic Chemistry, 89 (19), .
(doi:10.1021/acs.joc.4c01724).
Abstract
We report a de novo enantioselective synthesis of 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro-Dglycero-
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 crystallisation procedure and the absolute confirmation was ascertained by X-ray analysis. The synthetic route also allowed the access to the novel hexafluorinated heptose derivative 2,3,4-trideoxy-2,2,3,3,4,4- hexafluoro-L-threo-heptopyranose.
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Accepted/In Press date: 28 August 2024
e-pub ahead of print date: 13 September 2024
Identifiers
Local EPrints ID: 493908
URI: http://eprints.soton.ac.uk/id/eprint/493908
ISSN: 0022-3263
PURE UUID: 95cd5e81-274c-4b1f-8936-9c7f75c0b49a
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Date deposited: 17 Sep 2024 16:46
Last modified: 17 Oct 2024 01:36
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Contributors
Author:
Sébastien Depienne
Author:
Clement Q Fontenelle
Author:
Kristof Van Hecke
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