Chapter 6: Exo-glycals as useful tools for anomeric functionalization of sugars
Published:20 Mar 2014
N. Pellegrini-Moïse, M. Richard, and Y. Chapleur, in Carbohydrate Chemistry: Chemical and Biological Approaches, Volume 40, ed. A. Pilar Rauter, T. Lindhorst, and Y. Queneau, The Royal Society of Chemistry, 2014, vol. 40, ch. 6, pp. 99-117.
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Exo-glycals or C-glycosylidene compounds having an exocyclic double bond at the anomeric centre are readily available from sugar lactones through direct olefination reactions. These unsaturated carbohydrates proved useful intermediates. In this chapter are described recent studies from our group on functionalization or addition reactions on the double bond allowing the transformation of exo-glycals into more complex exo-glycals, spiroheterocycles, C-glycosyl, bis-C-glycosyl compounds and sugar β- and γ-amino acids of interest.