Facile synthesis of 2-C-methyl-D-arabino-gamma-1,4-lactones and mechanism study
文献类型：期刊论文
| 作者 | Lv, Bingqing4; Guo, Shuang1,3; Zhu, Fuqiang2; Hu, Tianwen2; Guo, Qi1,3; Lin, Haixia4; Xie, Yuanchao1,3; Shen, Jingshan1,3
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| 刊名 | TETRAHEDRON LETTERS
 |
| 出版日期 | 2018-04-11 |
| 卷号 | 59期号:15页码:1473-1475 |
| 关键词 | Nucleoside 2-C-Methyl-D-arabino-gamma-lactone Mechanism SN2 reaction O-18-labelled DMSO |
| ISSN号 | 0040-4039 |
| DOI | 10.1016/j.tetlet.2018.03.007 |
| 文献子类 | Article |
| 英文摘要 | In our previous research on the synthesis of 3,5-di-O-benzoyl-2-C-methyl-D-arabino-gamma-lactone 4a, the reaction mechanism of DMSO-mediated configuration inversion of C2 hydroxyl group in the lactone was ambiguous. As a follow-up to this research, we used O-18-labelled H2O and DMSO to investigate the mechanism. It was surprisingly discovered that DMSO served as an oxygen donor to stereoselectively displace the leaving group, and was regenerated in the reaction. The protecting groups had no influence on the inversion, but would significantly affect the yield. We also disclosed another approach for the synthesis of 4a without using the expensive Tf2O, which was more suitable for application. (C) 2018 Elsevier Ltd. All rights reserved. |
| WOS关键词 | HEPATITIS-C VIRUS ; SULFOXIDE-CARBODIIMIDE REACTIONS ; DIMETHYL-SULFOXIDE ; NUCLEOTIDE PRODRUG ; OXIDATION REACTION ; INHIBITORS ; HCV ; NUCLEOSIDE ; POLYMERASE ; DISCOVERY |
| 资助项目 | National Science Foundation for Young Scientists of China[21502209] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000430766400007 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/279805]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Lin, Haixia; Xie, Yuanchao |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 2.Topharman Shanghai Co Ltd, 388 Jialilue Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China 3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China; 4.Shanghai Univ, Dept Chem, Coll Sci, Innovat Drug Res Ctr, 99 Shangda Rd, Shanghai 200444, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Lv, Bingqing,Guo, Shuang,Zhu, Fuqiang,et al. Facile synthesis of 2-C-methyl-D-arabino-gamma-1,4-lactones and mechanism study[J]. TETRAHEDRON LETTERS,2018,59(15):1473-1475. |
| APA | Lv, Bingqing.,Guo, Shuang.,Zhu, Fuqiang.,Hu, Tianwen.,Guo, Qi.,...&Shen, Jingshan.(2018).Facile synthesis of 2-C-methyl-D-arabino-gamma-1,4-lactones and mechanism study.TETRAHEDRON LETTERS,59(15),1473-1475. |
| MLA | Lv, Bingqing,et al."Facile synthesis of 2-C-methyl-D-arabino-gamma-1,4-lactones and mechanism study".TETRAHEDRON LETTERS 59.15(2018):1473-1475. |
入库方式： OAI收割
来源：上海药物研究所
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