Collect. Czech. Chem. Commun. 2000, 65, 1145-1155

Glycosylation of 1-Aminoimidazole-2(3H)-thiones

Irene M. Lagoja, Arthur Van Aerschot, Chris Hendrix and Piet Herdewijn*

Laboratory of Medicinal Chemistry, Rega Institute, Minderbroedersstraat 10, B-3000 Leuven, Belgium


The selectivity of the glycosylation of 1-aminoimidazole-2(3H)-thiones can be controlled. Depending on the chosen conditions, either the kinetically favored S-glycosides or the thermodynamically more stable N-glycosylated compounds are obtained in only one anomeric configuration (β-anomer).

Keywords: 1-Aminoimidazole-2(3H)-thiones; Nucleosides; Glycosylations; Glycosidations; Ribosides; Imidazoles.

References: 24 live references.