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

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.

Domains: Chemical Sciences

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, 2017, 82 (5), pp.2753-2763. ⟨10.1021/acs.joc.6b03071⟩. ⟨hal-02046270⟩