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A synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose

A synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose
A synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose
There is an increasing interest in investigating how polyfluorination of carbohydrates modifies their physical and biological properties. An example that has caught much attention is 2,3,4-trideoxy-2,3,4-trifluoroglucose. Four syntheses of this compound have been reported, which are either low yielding, or long (13 or more steps). We report a 6-step synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose starting from levoglucosan. The solution-phase structure of an intermediate, 1,6-anhydro-2,4-dideoxy-2,4-difluoroallose, features a rare example of a bifurcated F···HO···F hydrogen bond, and is compared to its crystal structure.
0022-3263
Quiquempoix, Lucas G.
1664af14-ee65-4888-884b-5331983a25ba
Wang, Zhong
fe914552-33f1-4f0a-b8a1-52b82e8cb89e
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
Latchem, Peter G.
eb9e196a-9eda-461e-8585-b46e7264ed8e
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Le Questel, Jean-Yves
38aea4ae-64a3-43b7-8049-ea2f351459f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Quiquempoix, Lucas G.
1664af14-ee65-4888-884b-5331983a25ba
Wang, Zhong
fe914552-33f1-4f0a-b8a1-52b82e8cb89e
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
Latchem, Peter G.
eb9e196a-9eda-461e-8585-b46e7264ed8e
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Le Questel, Jean-Yves
38aea4ae-64a3-43b7-8049-ea2f351459f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Quiquempoix, Lucas G., Wang, Zhong, Graton, Jérôme, Latchem, Peter G., Light, Mark, Le Questel, Jean-Yves and Linclau, Bruno (2019) A synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose. Journal of Organic Chemistry. (doi:10.1021/acs.joc.9b00310).

Record type: Article

Abstract

There is an increasing interest in investigating how polyfluorination of carbohydrates modifies their physical and biological properties. An example that has caught much attention is 2,3,4-trideoxy-2,3,4-trifluoroglucose. Four syntheses of this compound have been reported, which are either low yielding, or long (13 or more steps). We report a 6-step synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose starting from levoglucosan. The solution-phase structure of an intermediate, 1,6-anhydro-2,4-dideoxy-2,4-difluoroallose, features a rare example of a bifurcated F···HO···F hydrogen bond, and is compared to its crystal structure.

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Linclau trifluoroglucose corrections v6_2 - Accepted Manuscript
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Accepted/In Press date: 14 March 2019
e-pub ahead of print date: 14 March 2019

Identifiers

Local EPrints ID: 429161
URI: http://eprints.soton.ac.uk/id/eprint/429161
ISSN: 0022-3263
PURE UUID: 3c457a68-c87a-4293-b1f1-7e2433e25325
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 22 Mar 2019 17:30
Last modified: 26 Nov 2021 05:51

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Contributors

Author: Lucas G. Quiquempoix
Author: Zhong Wang
Author: Jérôme Graton
Author: Peter G. Latchem
Author: Mark Light ORCID iD
Author: Jean-Yves Le Questel
Author: Bruno Linclau ORCID iD

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