Syntheses of sulfur-containing nucleoside analogs.
Reaction of glycosyl isothiocyanates (1a,b,c) with diazo compounds or chloroethylamine gave glycosylamino-1,2,3-thiadiazoles and glycosylimidazolidine-2-thiones. Similar reaction of 1a,b with ethanolamine afforded N-glycosyl-N'-hydroxyethylthioureides, followed by treatment of thionyl chloride to give glycosyliminothiazolidines. N-Glycosyl-N'-amidionthiocarboxamides were treated with thionyl chloride to give glycosyl s-triazin S-oxides. N-Glycosyl-N'-(6-amino-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)thioureides were oxidized with NBS into pyrimidotriazine glycosides.
D006601:Hexoses; D007202:Indicators and Reagents; D008722:Methods; D009705:Nucleosides / Q000138:chemical synthesis*; D010429:Pentoses; D013329:Structure-Activity Relationship; D013861:Thiocyanates
D006601:Hexoses; D007202:Indicators and Reagents; D009705:Nucleosides; D010429:Pentoses; D013861:Thiocyanates