Tunable Approach for the Stereoselective Synthesis of 1-C-Diethylphosphono(difluoromethyl) Iminosugars as Glycosyl Phosphate Mimics - Normandie Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2017

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

C. Cocaud
  • Function : Author
C. Nicolas
  • Function : Author
C.Y. Legault
  • Function : Author
O.R. Martin
  • Function : Author

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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Dates and versions

hal-02046270 , version 1 (22-02-2019)

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