Experimental and theoretical study of the conformational, vibrational and magnetic properties of 4,6-di-O-acetyl-2,3-dideoxy-D-threo-hex-2-enopyranosyl ethanesulfonamide

M LUJÁN ALEGRE; REINALDO PIS DIEZ; P.A. COLINAS

Journal of Molecular Structure

Elsevier

Año: 2009 vol. 919 p. 223 - 226

It is claimed that some recent N-glycosyl sulfonamides exhibit important biological activity. In particular,the title sulfonamide shows activity against lung carcinoma. It has been obtained elsewhere as an anomericmixture, in which the a form predominates. The 1H and 13C NMR spectra were also recorded. Presentcalculations carried out in the framework of the density functional theory, show that the b anomerform should be thermodynamically more stable than the a one. The relative stability could be associatedin principle to some particular intramolecular hydrogen bonds. As those results are in contrast withexperimental findings, they suggest that the synthesis of the title compound takes place under kineticcontrol mainly. The IR spectrum of the title N-glycosyl sulfonamide is recorded in the present workand theoretical calculations are performed to aid in the assignment of both the NMR and IR spectra.