钯催化立体选择性合成硝基烷类β-碳糖苷
收稿日期: 2023-03-14
修回日期: 2023-05-08
网络出版日期: 2023-05-30
基金资助
国家自然科学基金(22207063); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(D20015); 湖北省自然科学基金(2022CFB838); 湖北省教育厅(D20221204); 湖北省教育厅(Q20221212)
Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides
Received date: 2023-03-14
Revised date: 2023-05-08
Online published: 2023-05-30
Supported by
National Natural Science Foundation of China(22207063); Programme of Introducing Talents of Discipline to Universities (111 Project); Programme of Introducing Talents of Discipline to Universities(D20015); Hubei Provincial Natural Science Foundation(2022CFB838); Educational Commission of Hubei Province(D20221204); Educational Commission of Hubei Province(Q20221212)
碳糖苷因其优异的生理活性及耐水解/酶解特性, 在医学和生物学领域的研究中受到越来越多的关注, 但合成过程中仍面临着立体选择性的控制等挑战. 报道了一种3,4-O-碳酸酯烯糖和硝基化合物在双乙酰丙酮钯和1,4-双(二苯膦)丁烷(DPPB)配体的催化作用下, 室温反应得到具有高立体选择性的β-碳糖苷的方法, 且已由核磁共振(NMR)、高分辨质谱(HRMS)以及X射线单晶衍射等方法确定目标化合物的结构. 该方法具有广泛的底物范围, 对含吸电子基或供电子基的硝基烷类化合物都有很好的兼容性, 能以高产率得到单一β构型的碳糖苷, 为快速构建碳苷化合物库提供了可靠方法.
王兢睿 , 冯永奎 , 王能中 , 黄年玉 , 姚辉 . 钯催化立体选择性合成硝基烷类β-碳糖苷[J]. 有机化学, 2023 , 43(9) : 3216 -3225 . DOI: 10.6023/cjoc202303019
C-Glycosides have attracted more and more attention in the field of medicine and biology due to their excellent physiological activities and stability to hydrolysis/enzymolysis. However, the challenges of stereoselective control are still high during the synthesis process. In this paper, a method for preparing β-C-glycosides with high stereoselectivity through the reaction of 3,4-O-carbonate-D-galactal and nitroalkane with Pd(acac)2 and 1,4-bis(diphenylphosphino)butane (DPPB) ligand at room temperature has been reported. The structures of the target compounds have been determined by nuclear magnetic resonance spectroscopy (NMR), high-resolution mass spectra (HRMS) and X-ray single crystal diffraction. The method has a wide range of substrates, and has good compatibility for both electron-withdrawing and electron-donating nitroalkanes. Single β-C-glycosides were obtained with high yields, which provide a reliable method for the rapid construction of C-glycoside libraries.
Key words： glycals; stereoselectivity; C-galactosides; C-glycosylation; palladium catalysis
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