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

Chloé Cocaud; Cyril Nicolas; Thomas Poisson; Xavier Pannecoucke; Claude Y Legault; Olivier R Martin

doi:10.1021/acs.joc.6b03071

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

J Org Chem. 2017 Mar 3;82(5):2753-2763. doi: 10.1021/acs.joc.6b03071. Epub 2017 Feb 21.

Authors

Chloé Cocaud¹, Cyril Nicolas¹, Thomas Poisson², Xavier Pannecoucke², Claude Y Legault³, Olivier R Martin¹

Affiliations

¹ Institut de Chimie Organique et Analytique, UMR 7311, Université d'Orléans et CNRS , Rue de Chartres, BP 6759, 45067 Orléans cedex 2, France.
² Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen; INSA Rouen; CNRS , 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France.
³ Department of Chemistry, Centre in Green Chemistry and Catalysis, University of Sherbrooke , 2500 boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada.

PMID: 28221798
DOI: 10.1021/acs.joc.6b03071

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.

Publication types

Research Support, Non-U.S. Gov't