Dataset for: Structural study of 1-(2´, 3´-<i>O</i>-isopropylidene-(α-D-allo and –β-L-talofuranosyluron)-5´-cyanohydrin)uracil stereoisomers by NMR spectroscopy and theoretical methods.

The stereochemistry of nucleoside derivatives determines their pharmacological activity such as anticancer, antiviral, against human immunodeficiency virus (HIV) and antimycotic. Therefore, it is necessary to elucidate the structure of each stereoisomer. The isolation and spectroscopic characterization of the 1-(2´, 3´-<i>O</i>-isopropylidene-(α-D-allo and -β-L-talofuranosyluron)-5´-cyanohydrin)uracil stereoisomer is of great importance because these compounds are intermediaries in the development of novel nucleoside derivatives. In this study, we elucidated the structure of 5´(<i>R</i>) and (<i>S</i>)-cyanohydrin stereoisomers by NMR spectroscopy and tridimensional analysis. The structure was modeled based on the conformer with the local minimized energy. 1D-NOESY gave a detailed information about the tridimensional structure of each diastereoisomer. The ratio of the diastereoisomers determined by NMR, using DMSO-d<sub>6</sub> as solvent, was 65% of 5´(<i>R</i>)-cyanohydrin (<b>A</b>) and 35% of 5´(<i>S</i>)-cyanohydrin (<b>B</b>).