This research reports a novel method for synthesizing new thiazole thioglycosides. This series of thiazole thioglycosides were designed by the reaction of potassium cyanocarbonimidodithioate 2 with benzoyl acetonitrile 3a and ethyl bromoacetate 3b in the presence of ethanol-KOH to give the corresponding potassium 4-amino-5-substituted-thiazole-2-thiolates 4a,b. The latter compounds were treated with peracetylated sugar bromides 6a,b in DMF to give high yields of the corresponding thiazole thioglycosides 7a-d. Treatment of thiazole salts 4a,b with hydrochloric acid gave the corresponding 3-mercaptothiazole derivatives 5a,b. The latter compounds were reacted with peracetylated sugars 6 in sodium hydride in DMF to produce the S-glycosyl compounds 7a-d. Ammonolysis of the protected thiazole thioglycosides 6a-h gave the corresponding free thiazole thioglycosides 8a-d. The compounds have been characterized by 13C NMR, 1H NMR, and IR.

中文翻译：

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糖基化反应中的噻唑：噻唑硫糖苷的新合成

本研究报告了一种合成新型噻唑硫糖苷的新方法。该系列噻唑硫糖苷是通过氰基碳亚氨基二硫代酸钾 2 与苯甲酰乙腈 3a 和溴乙酸乙酯 3b 在乙醇-KOH 存在下反应得到相应的 4-氨基-5-取代-噻唑-2-硫醇钾 4a,b 而设计的. 后一种化合物在 DMF 中用全乙酰化糖溴化物 6a、b 处理，得到高产率的相应噻唑硫糖苷 7a-d。用盐酸处理噻唑盐4a、b，得到相应的3-巯基噻唑衍生物5a、b。后一种化合物在 DMF 中的氢化钠中与全乙酰化糖 6 反应以产生 S-糖基化合物 7a-d。受保护的噻唑硫糖苷 6a-h 的氨解得到相应的游离噻唑硫糖苷 8a-d。这些化合物已通过 13C NMR、1H NMR 和 IR 表征。