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Hydrozirconation/bromination, followed by a Michaelis-Arbuzov reaction, as a convenient approach towards polyfunctional glycosylphosphonates.
Joosten, Antoine; Heis, Floriane; Gavel, Marine; Chassagne, Véronique; Le Foll, Alexandra; Mébarki, Kévin; Gallienne, Estelle; Martin, Olivier R; Lecour, Thomas.
Affiliation
  • Joosten A; Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000, Rouen, France.
  • Heis F; Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000, Rouen, France.
  • Gavel M; Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000, Rouen, France.
  • Chassagne V; Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000, Rouen, France.
  • Le Foll A; Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000, Rouen, France.
  • Mébarki K; Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000, Rouen, France.
  • Gallienne E; Institut de Chimie Organique et Analytique (ICOA), UMR 7311, Université d'Orléans et CNRS, Rue de Chartres, BP, 6759, Orléans Cedex 2, France.
  • Martin OR; Institut de Chimie Organique et Analytique (ICOA), UMR 7311, Université d'Orléans et CNRS, Rue de Chartres, BP, 6759, Orléans Cedex 2, France.
  • Lecour T; Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA UMR 6014, 76000, Rouen, France. Electronic address: thomas.lecourt@insa-rouen.fr.
Carbohydr Res ; 499: 108228, 2021 Jan.
Article in En | MEDLINE | ID: mdl-33429168
ABSTRACT
In this note, an hydrozirconation/bromination/Michaelis-Arbuzov sequence was developped to introduce a trimethylene phosphonate unit on ketopyranosides. Performed on polyfunctional substrates bearing orthogonal protecting groups, this new approach provided a straightforward entry towards a large diversity of glycophosphomimetics having a quaternary anomeric position.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Organophosphorus Compounds Language: En Journal: Carbohydr Res Year: 2021 Document type: Article Affiliation country: France
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Organophosphorus Compounds Language: En Journal: Carbohydr Res Year: 2021 Document type: Article Affiliation country: France