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Facile Synthesis of Novel Benzoylthiophene C-Nucleoside Analogues via Coupling of Sugar Alkynes, Aroyl Chlorides, and 1,4-Dithiane-2,5-diol
Synthesis ( IF 2.2 ) Pub Date : 2020-01-30 , DOI: 10.1055/s-0039-1690808 Yang Luo 1 , Fei Gao 1 , Hong Liu 1 , Fuyi Zhang 1 , Yufen Zhao 1, 2
Synthesis ( IF 2.2 ) Pub Date : 2020-01-30 , DOI: 10.1055/s-0039-1690808 Yang Luo 1 , Fei Gao 1 , Hong Liu 1 , Fuyi Zhang 1 , Yufen Zhao 1, 2
Affiliation
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Concise synthesis of novel benzoylthiophene C-nucleoside analogues has been achieved by the reaction of various terminal sugar alkynes with substituted benzoyl chlorides and 1,4-dithiane-2,5-diol, and subsequent dilute HCl-promoted dehydration in one pot. The sugar alkynes include pyranosides, furanosides, and acyclic sugar. The benzoyl chloride has various substituents. Twenty-eight examples are given. The desired products are obtained in 70–89% yields, and the mechanism has been clarified by isolation of the intermediate.
中文翻译：
通过糖炔烃，芳酰氯和1,4-二硫代-2,5-二醇的偶联轻松合成新型苯甲酰噻吩C-核苷类似物
通过使各种末端糖炔与取代的苯甲酰氯和1,4-二噻吩-2,5-二醇反应，然后在一个罐中用稀盐酸促进的脱水反应，可以轻松合成新型苯甲酰基噻吩C-核苷类似物。糖炔包括吡喃糖苷，呋喃糖苷和无环糖。苯甲酰氯具有各种取代基。给出了二十八个例子。所需产物的收率为70-89％，并且通过分离中间体可以澄清其机理。
更新日期：2020-01-31
中文翻译：
通过糖炔烃，芳酰氯和1,4-二硫代-2,5-二醇的偶联轻松合成新型苯甲酰噻吩C-核苷类似物
通过使各种末端糖炔与取代的苯甲酰氯和1,4-二噻吩-2,5-二醇反应，然后在一个罐中用稀盐酸促进的脱水反应，可以轻松合成新型苯甲酰基噻吩C-核苷类似物。糖炔包括吡喃糖苷，呋喃糖苷和无环糖。苯甲酰氯具有各种取代基。给出了二十八个例子。所需产物的收率为70-89％，并且通过分离中间体可以澄清其机理。
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