New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2022-01-01 DOI:10.1080/07328303.2022.2039685

Nuha S. Kareem , Shaymaa A. Mohammed , May Jaleel Abed , Asaad H. Aneed , Hayder M. Kamal , N. Idayu Zahid , Karem J. Sabah

引用次数: 0

Abstract

A series of new macrocycles based on alkyl glycosides derived from D-glucose and D-galactose was synthesized. The macrocycles were easily obtained by the reaction of dialkynyl derivatives with diazides via copper-catlyzed 1,3-cycloaddition reaction. Simple protecting group strategies were applied to obtain the vicinal dihydroxy derivatives, followed by Williamson etherification with propargyl bromides to get the dialkynyl derivatives. These derivatives were subjected to 1,3-Hüisgen triazole coupling with diazides furnishing the macrocycles in good yields. The 1,3-Hüisgen reaction used to build these macrocycles was investigated thoroughly with respect to reaction time, catalysts, solvents, and temperature for optimum macrocyclisation.

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通过铜催化的三唑偶联结合糖脂的新大环

摘要以D-葡萄糖和D-半乳糖为原料，合成了一系列新的大环化合物。通过铜催化的1，3-环加成反应使二芳基衍生物与二叠氮化物反应，容易获得大环。采用简单的保护基策略得到邻位二羟基衍生物，然后用溴丙炔进行Williamson醚化反应得到二烷基衍生物。将这些衍生物与二叠氮化物进行1,3-Hüisgen三唑偶联，以高产率提供大环。从反应时间、催化剂、溶剂和最佳大环化温度等方面对用于构建这些大环的1,3-Hüisgen反应进行了彻底研究。图形摘要

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.