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Amidoximes α-Hydroxylées Dérivées de Sucres

1986; Taylor & Francis; Volume: 5; Issue: 4 Linguagem: Inglês

10.1080/07328308608062981

1532-2327

Jean M. J. Tronchet, Guido Zosimo‐Landolfo, Gérald Bernardinelli, Philippe Arrizabalaga, Michel Geoffrey,

Structural and Chemical Analysis of Organic and Inorganic Compounds

Abstract The two epimeric α-hydroxyamidoximes 5 and 6 - and some derivatives thereof, particularly oxadiazoles 16 and 17 - have been stereospecifically prepared from the keto sugar 1. Compound 5 was found to exist in two polymorphous crystalline forms (α and β) depending on the crystallization solvent. Both forms are orthorhombic, space group P212121 (α-form : a = 10.408(3), b = 10.559(2), c = 14.144(2) Å; β-form : a = 7.890(1), b = 10.305(2), c = 19.064(4) Å). The calculation of pseudorotation parameters showed that each polymorph is associated with a slightly different conformation of the dioxolane rings. The Oacetyl derivative 11 of 6 adopts a different conformation of the furanose ring. In the three structures, a network of hydrogen bonds exists. The amidoxime 5 forms a cupric complex [Cu(5)2] whose ESR spectrum proved its square structure.