Ogura H, Takahashi H, Sato O
Nucleic Acids Symp Ser. 1980(8):s1-4.
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.
异硫氰酸糖基酯（1a、b、c）与重氮化合物或氯乙胺反应生成糖基氨基-1,2,3-噻二唑和糖基咪唑烷-2-硫酮。1a、b与乙醇胺的类似反应得到N-糖基-N'-羟乙基硫脲，随后用亚硫酰氯处理得到糖基亚氨基噻唑烷。N-糖基-N'-氨基硫代甲酰胺用亚硫酰氯处理得到糖基s-三嗪S-氧化物。N-糖基-N'-(6-氨基-1,3-二甲基-2,4-二氧代嘧啶-5-基)硫脲用N-溴代琥珀酰亚胺氧化成嘧啶三嗪糖苷。
