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

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

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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