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Journal Articles Journal of Organic Chemistry Year : 2019

Synthesis of 2,3,4-Trideoxy-2,3,4-trifluoroglucose

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...H(O)...F hydrogen bond and is compared to its crystal structure.
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hal-02419527 , version 1 (14-06-2024)

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Lucas Quiquempoix, Zhong Wang, Jérôme Graton, Peter G. Latchem, Mark Light, et al.. Synthesis of 2,3,4-Trideoxy-2,3,4-trifluoroglucose. Journal of Organic Chemistry, 2019, 84 (9), pp.5899-5906. ⟨10.1021/acs.joc.9b00310⟩. ⟨hal-02419527⟩
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