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Straightforward Preparation of Functionalized α-CF2-Galactosides through an Oxygen to Carbon Acyl Migration

Authors

  • Sophie Colombel,

    1. UMR6014 & FR3038-IRCOF, CNRS, Université et INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France), Fax: (+33) 2-35-52-29-59
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  • Morgane Sanselme,

    1. UPRES EA 3233, Université de Rouen, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France)
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  • Dr. Eric Leclerc,

    Corresponding author
    1. UMR6014 & FR3038-IRCOF, CNRS, Université et INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France), Fax: (+33) 2-35-52-29-59
    • UMR6014 & FR3038-IRCOF, CNRS, Université et INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France), Fax: (+33) 2-35-52-29-59
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  • Prof. Dr. Jean-Charles Quirion,

    1. UMR6014 & FR3038-IRCOF, CNRS, Université et INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France), Fax: (+33) 2-35-52-29-59
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  • Prof. Dr. Xavier Pannecoucke

    1. UMR6014 & FR3038-IRCOF, CNRS, Université et INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France), Fax: (+33) 2-35-52-29-59
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Abstract

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A privileged Glycon! A radical-addition Meerwein–Ponndorf–Verley (MPV) reduction sequence provides access to functionalized α-CF2-galactosides (see scheme). Introduction of a CF2Br group in the pseudo-anomeric position aided the transfer of an aglycon chain from O-2 to C-1′ through an intramolecular addition–reduction sequence, which involved a Br–Li exchange. This methodology gives access to a wide range of fluorinated C-glycosidic analogues of glycoconjugates.

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