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Synthesis 2022; 54(15): 3414-3420
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
,
Maciej Malinowski  ‡
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
› Author AffiliationsM.M. and A.F. thank the Fondation de la Maison de la Chimie for financial support.
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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.

Key words

phosphonylation - cross-coupling - 2-iodoglycals - palladium catalysis - glycoanalogues

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1709-3305.
  • Supporting Information


Publication History

Received: 15 October 2021

Accepted after revision: 30 November 2021

Accepted Manuscript online:
30 November 2021

Article published online:
26 January 2022

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