N-glycosides - 2. Structure of the products of the reaction of glycosyl isothiocyanates with 4-amino-4-methyl-2-pentanone

Article abstract of DOI:10.1007/BF00506158

The structures of N-glycosides obtained by the reaction of 2,3,4,6-tetra-O-acetyl-β-D-gluco(galacto)pyranosyl isothiocyanates with 4-amino-4-methyl-2-pentanone and the structures of their deacetylation products were established by means of IR, UV, and PMR spectroscopy. The glycosides have primarily the N₁-glycosyl-N₃-(4-methyl-2-oxo-4-pentyl)-thiourea structure, which exists in a state of prototropic ring-chain tautomerism with cyclic tautomers, viz., 3-glycosyl-4,4,6-trimethyl-4-hydroxyhexahydropyrimidine-2-thiones.