Hydrozirconation/bromination, followed by a Michaelis-Arbuzov reaction, as a convenient approach towards polyfunctional glycosylphosphonates

Antoine Joosten (1) , Floriane Heis (1) , Marine Gavel (1) , Véronique Chassagne (1) , Alexandra Le Foll (1) , Kévin Mébarki (1) , Estelle Gallienne (2) , Olivier A.J. Martin (2) , Thomas Lecour (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 ICOA - Institut de Chimie Organique et Analytique

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.

Domaines: Chimie

Antoine Joosten, Floriane Heis, Marine Gavel, Véronique Chassagne, Alexandra Le Foll, et al.. Hydrozirconation/bromination, followed by a Michaelis-Arbuzov reaction, as a convenient approach towards polyfunctional glycosylphosphonates. Carbohydrate Research, 2020, ⟨10.1016/j.carres.2020.108228⟩. ⟨hal-03151446⟩