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

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 anomeric mixture, in which the α form predominates. The 1H and 13C NMR spectra were also recorded. Present calculations carried out in the framework of the density functional theory, show that the β anomer form should be thermodynamically more stable than the α one. The relative stability could be associated in principle to some particular intramolecular hydrogen bonds. As those results are in contrast with experimental findings, they suggest that the synthesis of the title compound takes place under kinetic control mainly. The IR spectrum of the title N-glycosyl sulfonamide is recorded in the present work and theoretical calculations are performed to aid in the assignment of both the NMR and IR spectra.