A new approach for the N- and S-galactosylation of 5-arylidene-2-thioxo-4-thiazolidinones

Abstract N- and S-galactosylation was carried out via the reaction of 5-(( Z )-arylidene)-2-thioxo-4-thiazolidinones with 2,3,4,6-tetra- O -acetyl-α- d -galactopyranosyl bromide under alkaline conditions or under silylation conditions. Deacetylation of the N-galactosylation products was performed with concentrated hydrochloric acid in methanol (3.5%) or sodium methoxide in methanol without cleavage of the 2-thioxo-4-thaizolidinone ring by means of acid hydrolysis. The anomers were separated by flash column chromatography, and their configurations were assigned by NMR spectroscopy. The deprotected nucleosides were screened against leukemia L-1210 and were found inactive.