Synthesis
DOI: 10.1055/a-1709-3305
special topic
Bürgenstock Special Section 2021 – Future Stars in Organic Chemistry

Hirao Cross-Coupling Reaction as an Efficient Tool to Build Non-natural C2-Phosphonylated Sugars

Olivier Monasson
a   CY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France
b   Université Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France
,
a   CY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France
c   Faculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warsaw, Poland
,
Nadège Lubin-Germain
a   CY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France
b   Université Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France
,
Angélique Ferry
a   CY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France
b   Université Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France
› Institutsangaben
M.M. and A.F. thank the Fondation de la Maison de la Chimie for financial support.


Abstract

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 the creation of 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 applying this methodology. Deprotection conditions are also described.

Supporting Information



Publikationsverlauf

Eingereicht: 15. Oktober 2021

Angenommen nach Revision: 30. November 2021

Publikationsdatum:
30. November 2021 (online)

© 2021. Thieme. All rights reserved

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