Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Saensook, Chonburi, 20131, Thailand.
Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Saensook, Chonburi, 20131, Thailand.
Carbohydr Res. 2019 Oct 1;484:107780. doi: 10.1016/j.carres.2019.107780. Epub 2019 Aug 19.
This work combined three classes of compounds in the same molecule "amino triazole-glycoside" and developed a convenient method for the synthesis of this type of compound via a one-pot two step reaction. Alkylation of amine derivatives with propargyl bromide to give propargylamine was performed in the first step subsequently followed by a 'click' reaction with various β-azido-glycosides in the presence of CuI in aqueous solution to provide β-amino triazole-glycosides. Thirty-two examples of glycosides were obtained in moderate to good yield using this one-pot procedure.
这项工作将三类化合物“氨基三唑-糖苷”结合在同一个分子中，并开发了一种通过一锅两步反应方便合成此类化合物的方法。第一步是用炔丙基溴对胺衍生物进行烷基化，得到炔丙胺，然后在水溶液中加入碘化亚铜，与各种β-叠氮糖苷进行“点击”反应，得到β-氨基三唑-糖苷。通过这种一锅法，得到了 32 个糖苷的中等至良好产率的实例。
