Stereoselective N-glycosylation with N-4-acyl cytosines and efficient synthesis of gemcitabine
文献类型：期刊论文
| 作者 | Liu, Tongchao2,3; Tang, Jiadeng4; Liang, Jianpeng3,4; Chen, Yabin3,4; Wang, Xiaowen3; Shen, Jingkang3,5; Zhao, Dongmei2; Xiong, Bing3,5 ; Cen, Jun-Da1; Chen, Yue-Lei3,5
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| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2019-03-01 |
| 卷号 | 75期号:9页码:1203-1213 |
| 关键词 | Stereoselective N-glycosylation N-4-acyl cytosine Nucleoside Gemcitabine |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2019.01.027 |
| 通讯作者 | Zhao, Dongmei(dongmeiz-67@163.com) ; Xiong, Bing(bxiong@simm.ac.cn) ; Cen, Jun-Da(cjd@hansoh.cn) ; Chen, Yue-Lei(chenyuelei@gmail.com) |
| 英文摘要 | Through systematical comparison of various N-4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N-4-Bz cytosine and anomeric mixture of 2,2'-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N-4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine. (C) 2019 Elsevier Ltd. All rights reserved. |
| WOS关键词 | NUCLEOSIDES ; PSI-6130 |
| 资助项目 | National Natural Science Foundation of China[21877121] ; National Natural Science Foundation of China[81673309] ; National Natural Science Foundation of China[81330076] ; National Natural Science Foundation of China[81703544] ; Personalized Medicines - Molecular Signature-based Drug Discovery and Development, Strategic Priority Research Program of the Chinese Academy of Sciences[XDA12020310] ; program for Innovative Research Team of the Ministry of Education ; program for Liaoning Innovative Research Team at Shenyang Pharmaceutical University |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000459522800012 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/290497]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Zhao, Dongmei; Xiong, Bing; Cen, Jun-Da; Chen, Yue-Lei |
| 作者单位 | 1.Jiangsu Hansoh Pharmaceut Grp Co Ltd, 9 Dongjin Rd, Lianyungang 222069, Jiangsu, Peoples R China 2.Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, 103 Wenhua Lu, Shenyang 110016, Liaoning, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 4.Shanghai Famo Biotechnol Co Ltd, 1119 Landian Rd,2-502, Shanghai 201203, Peoples R China 5.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,et al. Stereoselective N-glycosylation with N-4-acyl cytosines and efficient synthesis of gemcitabine[J]. TETRAHEDRON,2019,75(9):1203-1213. |
| APA | Liu, Tongchao.,Tang, Jiadeng.,Liang, Jianpeng.,Chen, Yabin.,Wang, Xiaowen.,...&Chen, Yue-Lei.(2019).Stereoselective N-glycosylation with N-4-acyl cytosines and efficient synthesis of gemcitabine.TETRAHEDRON,75(9),1203-1213. |
| MLA | Liu, Tongchao,et al."Stereoselective N-glycosylation with N-4-acyl cytosines and efficient synthesis of gemcitabine".TETRAHEDRON 75.9(2019):1203-1213. |
入库方式： OAI收割
来源：上海药物研究所
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