Carbohydrate Chemistry: Chemical and Biological Approaches, Volume 45
Sonogashira cross-coupling on carbohydrate templates
Published:15 Dec 2021
Special Collection: 2021 ebook collection
R. F. N. Silva, S. Silva, P. Rollin, and A. P. Rauter, in Carbohydrate Chemistry: Chemical and Biological Approaches, Volume 45, ed. A. Pilar Rauter, T. K. Lindhorst, and Y. Queneau, The Royal Society of Chemistry, 2021, vol. 45, pp. 157-238.
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Recently introduced in glycochemistry, the Sonogashira cross-coupling reaction has shown a promising potential in connecting widely varied structural units with carbohydrate templates through alkynyl linkers. It has found many synthetic applications to develop biomolecule mimics, including carbohydrate-connected macrocycles, clusters/dendrimers containing carbohydrate units, functionalized glycals, C-glycosides and nucleosides. A diversity of Sonogashira synthetic strategies involving sugars, either equipped with a terminal alkyne segment or bearing a sp2 C-halide moiety, are herein reviewed, demonstrating the wide scope of Sonogashira reaction for the generation of biologically relevant carbohydrate-based molecules.