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; PEDRO A COLINAS

JOURNAL OF MOLECULAR STRUCTURE

Elsevier

Año: 2009 vol. 919 p. 223 - 226

0022-2860

It is claimed that some recent N-glycosyl sulfonamides exhibit important biologicalactivity. In particular, the title sulfonamide shows activity against lung carcinoma. It hasbeen obtained elsewhere as an anomeric mixture, in which the a form predominates.The 1H and 13C NMR spectra were also recorded. Present calculations carried out in theframework of the density functional theory, show that the b anomer form should bethermodynamically more stable than the a one. The relative stability could beassociated in principle to some particular intramolecular hydrogen bonds. As thoseresults are in contrast with experimental findings, they suggest that the synthesis of thetitle compound takes place under kinetic control mainly. The IR spectrum of the title Nglycosylsulfonamide is recorded in the present work and theoretical calculations areperformed to aid in the assignment of both the NMR and IR spectra.