Abstract
3-Deoxy-3-thioureido derivatives of 1,2:5,6- di-O- isopropylidene-α- d- allofuranose and 1,2:5,6- di-O- isopropylidene-α- d- glucofuranose were prepared, and their conformational properties in chloroform- d solutions were studied by temperature variable 1H NMR spectroscopy. The whole results, which include temperature coefficient data for the exchangeable pseudoamide protons, support that the presence of the sugar NHC( S) E-rotamer for d- gluco N, N′-disubstituted derivatives can be essentially ascribed to the existence of an intramolecular hydrogen bond analogous to that characteristic of peptide γ-turns.
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