Synthesis
DOI: 10.1055/a-1709-3305
special topic

Hirao cross-coupling reaction as efficient tool to build non-natural C2-phosphonylated sugars.

Olivier Monasson
1  Chemistry, CY Cergy Paris University, Cergy-Pontoise, France (Ringgold ID: RIN27004)
,
2  Chemistry, Warsaw University of Technology, Warszawa, Poland (Ringgold ID: RIN49566)
,
Nadége Lubin-Germnain
3  chemistry, Universite de Cergy-Pontoise UFR sciences et techniques, Cergy-Pontoise, France (Ringgold ID: RIN173493)
,
Angélique Ferry
4  Chimie, Universite de Cergy-Pontoise, Cergy-Pontoise, France (Ringgold ID: RIN27004)
› Author Affiliations
Supported by: Fondation de la Maison de la Chimie

A range of C2-phosphonylated sugars have been accessed through a palladium-catalyzed Hirao cross-coupling on 2-iodoglycals using trialkylphosphites as phosphorylating reagents. The developed conditions led to create an unnatural C-P bond on sugars and proved to be compatible with diversely protected glycals (acetyl-, benzyl-, PMB-protected) as well as with unprotected substrates. Several monosaccharides and one disaccharide have been synthesized by this methodology. Deprotection conditions were also described.



Publication History

Received: 15 October 2021

Accepted after revision: 30 November 2021

Publication Date:
30 November 2021 (online)

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