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

Olivier Monasson; Maciej Malinowski; Nadège Lubin-Germain; Angélique Ferry

doi:10.1055/a-1709-3305

Synthesis, Table of Contents

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

Authors

Olivier Monasson‡

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^bUniversité Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France
Maciej Malinowski ‡

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^cFaculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warsaw, Poland
Nadège Lubin-Germain

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^bUniversité Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France
Angélique Ferry∗

^aCY Cergy-Paris Université, BioCIS, CNRS, 5 mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France

^bUniversité Paris-Saclay, BioCIS, CNRS, 5, rue J-B Clément, 92296 Châtenay-Malabry cedex, France

Abstract

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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

Full Text

References

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Supplementary Material

Supporting Information (PDF)