Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction
文献类型：期刊论文
| 作者 | Liu, He3,6; Yang, Wenjiao2,4,5; Zheng, Shaojiu2,3; He, Yang2,3; Wang, Guan3; Qin, Hongjian1,2,4,5; Zhu, Fuqiang1; Jiang, Xiangrui2,3 ; Shen, Jingshan2,3; Gong, Xudong1
|
| 刊名 | TETRAHEDRON LETTERS
 |
| 出版日期 | 2022-04-13 |
| 卷号 | 95页码:6 |
| ISSN号 | 0040-4039 |
| 关键词 | Asymmetric synthesis Stereoselectivity Ribonolactone Evans-Aldol reaction |
| DOI | 10.1016/j.tetlet.2022.153728 |
| 通讯作者 | Gong, Xudong(gongxudong10@mails.ucas.ac.cn) |
| 英文摘要 | A convenient and novel route for the stereoselective synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-chloro-2-C-methyl-D-ribono-c-lactone 5a and its analogues is developed by an Evans-Aldol reaction in the presence of TiCl4. Starting from 2-chloropropionyl chloride, 5a is efficiently and regioselectively produced on a kilogram scale in an overall yield of 32% with an HPLC purity of 98% by area. In addition, this approach allowed an efficient synthesis of 3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribono-c- lactone 5b in a total 20% yield. (C)& nbsp;2022 Elsevier Ltd. All rights reserved. |
| WOS关键词 | CHIRAL AUXILIARIES ; NUCLEOSIDE ; ADDITIONS ; OXAZOLIDINONES ; POLYMERASE ; DISCOVERY ; PRODRUGS |
| 资助项目 | Shanghai Municipal Science and Technology Major Project[19430750100] ; Shanghai Science and Technology Committee in China |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| WOS记录号 | WOS:000792912100010 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/301047]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Gong, Xudong |
| 作者单位 | 1.Topharman Shanghai Co Ltd, Bldg 1,388 Jialilue Rd,Zhangjiang Hitech Pk, Shanghai 201209, Peoples R China 2.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 4.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Xinjiang Indigenous Med Plants Resource U, South Beijing Rd 40-1, Urumqi 830011, Xinjiang, Peoples R China 5.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Reg, South Beijing Rd 40-1, Urumqi 830011, Xinjiang, Peoples R China 6.Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Peoples R China |
| 推荐引用方式 GB/T 7714 |
Liu, He,Yang, Wenjiao,Zheng, Shaojiu,et al. Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction [J]. TETRAHEDRON LETTERS,2022,95:6. |
| APA |
Liu, He.,Yang, Wenjiao.,Zheng, Shaojiu.,He, Yang.,Wang, Guan.,...&Gong, Xudong.(2022). Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction .TETRAHEDRON LETTERS,95,6. |
| MLA |
Liu, He,et al." Stereoselective synthesis of 2-deoxy-2-disubstituted ribonolactones through a TiCl4-mediated Evans-Aldol reaction ".TETRAHEDRON LETTERS 95(2022):6. |
入库方式： OAI收割
来源：上海药物研究所
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