Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity
文献类型：期刊论文
| 作者 | Liu, Tongchao1,2; Zhu, Zhengdan3,4; Ren, Huanming2,5; Chen, Yabin2; Chen, Guohua5; Cheng, Maosheng1; Zhao, Dongmei1; Shen, Jingkang2,4; Zhu, Weiliang3,4 ; Xiong, Bing2,4
|
| 刊名 | ORGANIC CHEMISTRY FRONTIERS
 |
| 出版日期 | 2018-06-21 |
| 卷号 | 5期号:12页码:1992-1999 |
| ISSN号 | 2052-4129 |
| DOI | 10.1039/c8qo00165k |
| 文献子类 | Article |
| 英文摘要 | C-Nucleosides constitute a valuable class of compounds in biological and medicinal chemistry studies. We report herein a new and efficient synthesis of both alpha-and beta-C-nucleosides with high anomeric selectivity from N-6-Boc protected purine analogues. The synthetic approach features a carefully designed lithiation and silane reduction sequence. The anomeric stereochemistry outcome is dictated by the protecting group of sugar lactones. Computational studies suggest that previously neglected interactions between partially positively-charged silane and the substitutions on a sugar moiety play important roles in the anomeric selectivity of silane-mediated C-nucleoside synthesis. |
| WOS关键词 | RING OXOCARBENIUM IONS ; STEREOCONTROLLED SYNTHESIS ; GLYCOSYLIDENE CARBENES ; ADENOSINE DERIVATIVES ; STEREOSELECTIVITY ; OXACARBENIUM ; REDUCTION ; GUANOSINE ; DISCOVERY ; ANALOG |
| 资助项目 | National Natural Science Foundation of China[81673309] ; National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program", China[2014ZX09507-002] ; Personalized Medicines - Molecular Signature-based Drug Discovery and Development[00000000] ; Strategic Priority Research Program of the Chinese Academy of Sciences[XDA12020310] ; program for Innovative Research Team of the Ministry of Education[00000000] ; program for Liaoning Innovative Research Team at Shenyang Pharmaceutical University[00000000] ; Special Program for Applied Research on Super Computation of the NSFC-Guangdong Joint Fund (the second phase)[U1501501] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000435115200019 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/279700]  |
| 专题 | 药物化学研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 药物发现与设计中心 |
| 通讯作者 | Zhao, Dongmei; Zhu, Weiliang; Xiong, Bing; Chen, Yue-Lei |
| 作者单位 | 1.Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, 103 Wenhua Lu, Shenyang 110016, Liaoning, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Drug Discovery & Design Ctr, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 4.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China; 5.China Pharmaceut Univ, Sch Pharm, 24 Tongjiaxiang, Nanjing 210009, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Tongchao,Zhu, Zhengdan,Ren, Huanming,et al. Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity[J]. ORGANIC CHEMISTRY FRONTIERS,2018,5(12):1992-1999. |
| APA | Liu, Tongchao.,Zhu, Zhengdan.,Ren, Huanming.,Chen, Yabin.,Chen, Guohua.,...&Chen, Yue-Lei.(2018).Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity.ORGANIC CHEMISTRY FRONTIERS,5(12),1992-1999. |
| MLA | Liu, Tongchao,et al."Efficient syntheses of alpha- and beta-C-nucleosides and the origin of anomeric selectivity".ORGANIC CHEMISTRY FRONTIERS 5.12(2018):1992-1999. |
入库方式： OAI收割
来源：上海药物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。