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Synthesis of Unnatural Phosphonosugar Analogues.
Journal article   Peer reviewed

Synthesis of Unnatural Phosphonosugar Analogues.

Bénédicte Dayde, Claire Pierra, Gilles Gosselin, Dominique Surleraux, Amadou Tidjani Ilagouma, Coralie Laborde, Jean-Noël Volle, David Virieux and Jean-Luc Pirat
European Journal of Organic Chemistry, Vol.2014(6), pp.1333-1337
07/02/2014

Abstract

Medicinal chemistry Glyco­mimetics Bioisosteres Carbohydrates Phosphorus heterocycles
The first synthesis of new cyclic phosphonates (phostones), analogues of pentafuranoses containing a phosphorus atom in place of the anomeric carbon in the deoxyribose and deoxyxylose series, is described. Two methods, of respectively six and seven steps, were developed in parallel, and each gave the racemic phosphonosugars in good yields. Compounds analogous to the alpha and beta anomers were isolated and fully characterized by NMR spectroscopy.
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