Stereoselective addition of Grignard reagents to (2-methyl-5-tert-butyl)phenyl 1-thio-beta-D-ribopentodialdo-1,4-furanoside derivative
文献类型：期刊论文
| 作者 | Ren, Huanming1,2; Xie, Wuchen1,2; Xiong, Bing1,3 ; Shen, Jingkang1,3; Chen, Guohua2; Chen, Yue-Lei1,3
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| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2017-04-20 |
| 卷号 | 73期号:16页码:2290-2304 |
| 关键词 | Nucleophilic addition Stereoselective reaction Grignard reagents 5-C-Substituted ribofuranoside Mosher ester |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2017.03.013 |
| 文献子类 | Article |
| 英文摘要 | Addition of a wide range of Grignard reagents to acetone protected (2-methyl-5-tert-butyl)phenyl 1-thio-(beta-D-ribopentodialdo-1,4-furanoside 3b produced useful 5(R)-C-substituted products with moderate to good yields, and moderate to perfect stereoselectivities, with no need of additives. n.O.e. Analysis of 3b showed that 1-S-aryl group could contribute to the stereoselectivity of addition reaction. The stereo chemistry of 4 representative 5-C-substituted ribofuranoside products was further confirmed by NMR study of corresponding Mosher esters, by chemical derivatization, or by single crystal study. (C) 2017 Elsevier Ltd. All rights reserved. |
| WOS关键词 | ABSOLUTE-CONFIGURATION ; NONSENSE MUTATIONS ; O-METHYLMANDELATE ; CHEMICAL-SHIFTS ; INHIBITORS ; ALDEHYDES ; SELECTIVITY ; ALCOHOLS ; DESIGN ; POTENT |
| 资助项目 | National Natural Science Foundation of China[81673309] ; National Natural Science Foundation of China[81273368] ; National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program", China[2014ZX09507-002] ; "Personalized Medicines - Molecular Signature-based Drug Discovery and Development", Strategic Priority Research Program of the Chinese Academy of Sciences[XDA12020310] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000399630600014 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/272696]  |
| 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 |
| 通讯作者 | Chen, Guohua; Chen, Yue-Lei |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 2.China Pharmaceut Univ, Sch Pharm, 24 Tongjiaxiang, Nanjing 210009, Jiangsu, Peoples R China; 3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Ren, Huanming,Xie, Wuchen,Xiong, Bing,et al. Stereoselective addition of Grignard reagents to (2-methyl-5-tert-butyl)phenyl 1-thio-beta-D-ribopentodialdo-1,4-furanoside derivative[J]. TETRAHEDRON,2017,73(16):2290-2304. |
| APA | Ren, Huanming,Xie, Wuchen,Xiong, Bing,Shen, Jingkang,Chen, Guohua,&Chen, Yue-Lei.(2017).Stereoselective addition of Grignard reagents to (2-methyl-5-tert-butyl)phenyl 1-thio-beta-D-ribopentodialdo-1,4-furanoside derivative.TETRAHEDRON,73(16),2290-2304. |
| MLA | Ren, Huanming,et al."Stereoselective addition of Grignard reagents to (2-methyl-5-tert-butyl)phenyl 1-thio-beta-D-ribopentodialdo-1,4-furanoside derivative".TETRAHEDRON 73.16(2017):2290-2304. |
入库方式： OAI收割
来源：上海药物研究所
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