Chapter 12: Sucrose as chiral platform in the synthesis of macrocyclic receptors
Published:20 Mar 2014
S. Jarosz, M. A. Potopnyk, and M. Kowalski, 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. 12, pp. 236-256.
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This review presents the syntheses of different analogs of sucrose. Transformations of this di-saccharide at the terminal positions (C1′, or C6, or C6′) provide modified sucroses such as amines, uronic acids, thiols, or phosphorus derivatives. Preparation of so-called ‘higher sucroses’ i.e. derivatives in which the terminal positions are elongated by a polyhydroxylated carbon chain is also reviewed. Special attention is directed to the synthesis and properties of macrocyclic derivatives: crown- and aza-crown ethers with sucrose scaffold. Such macrocyclic receptors exhibit interesting complexing properties towards chiral ammonium salts.