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Tunable Approach for the Stereoselective Synthesis of 1-C-Diethylphosphono(difluoromethyl) Iminosugars as Glycosyl Phosphate Mimics

C. Cocaud C. Nicolas 1 Thomas Poisson 2 Xavier Pannecoucke 2 C.Y. Legault O.R. Martin
1 SSOLEIL - Synchrotron SOLEIL
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : An efficient methodology for the stereoselective and tunable addition of LiCF2P(O)(OEt)2 and BrMgCF2P(O)(OEt)2 reagents to N-t-butanesulfinyl glycosylamines is described with details on the stereochemical effects at play in this process. It provides a practical route to various 1-C-diethylphosphono(difluoromethyl) iminosugars as glycosyl phosphate and sugar nucleotide mimics.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046270
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:39:39 PM
Last modification on : Thursday, July 2, 2020 - 3:29:51 AM

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CNRS | COBRA | UNIROUEN | COMUE-NORMANDIE | INSA-ROUEN | INC-CNRS | SYNCHROTRON-SOLEIL | INSA-GROUPE | ENSICAEN | UNILEHAVRE | UNICAEN

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C. Cocaud, C. Nicolas, Thomas Poisson, Xavier Pannecoucke, C.Y. Legault, et al.. Tunable Approach for the Stereoselective Synthesis of 1-C-Diethylphosphono(difluoromethyl) Iminosugars as Glycosyl Phosphate Mimics. Journal of Organic Chemistry, American Chemical Society, 2017, 82 (5), pp.2753-2763. ⟨10.1021/acs.joc.6b03071⟩. ⟨hal-02046270⟩

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