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One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-cis glycosylamines bearing various protected groups

文献类型：期刊论文

作者Dong, Sanfeng1,2; Zhao, Yitian1,2; Shi, Yulong2,3; Xu, Zhijian2,3; Shen, Jingshan2,3; Jia, Qi1; Li, Yiming1; Chen, Kaixian1,2,3; Li, Bo2,3; Zhu, Weiliang1,2,3
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
出版日期2021-02-21
卷号19期号:7页码:1580-1588
ISSN号1477-0520
DOI10.1039/d0ob02477e
通讯作者Jia, Qi(q_jia@126.com) ; Li, Bo(boli@simm.ac.cn) ; Zhu, Weiliang(wlzhu@simm.ac.cn)
英文摘要Herein we disclosed a straightforward synthesis of oxazoline-fused saccharides (oxazolinoses) from peracetylated saccharides and benzonitriles under acidic conditions with stoichiometric amounts of water. The density functional theory (DFT) calculations have revealed the origin of the stereoselectivity and the key role of water in promoting the departure of the acetyl group at C-2. The resulting oxazolinoses can be concisely converted into the corresponding 1,2-cis glycosylamines bearing various protected groups, allowing the access to schisandrin derivatives.
资助项目National Natural Science Foundation of China[22077131] ; National Natural Science Foundation of China[81872797] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002] ; Natural Science Foundation of Shanghai, China[19ZR1467800]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000621563000015
出版者ROYAL SOC CHEMISTRY
源URL[http://119.78.100.183/handle/2S10ELR8/295574]  
专题中国科学院上海药物研究所
通讯作者Jia, Qi; Li, Bo; Zhu, Weiliang
作者单位1.Shanghai Univ Tradit Chinese Med, 1200 Cailun Rd, Shanghai 201203, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
3.Univ Chinese Acad Sci, Sch Pharm, 19A Yuquan Rd, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714		 Dong, Sanfeng,Zhao, Yitian,Shi, Yulong,et al. One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-cis glycosylamines bearing various protected groups[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2021,19(7):1580-1588.
APA Dong, Sanfeng.,Zhao, Yitian.,Shi, Yulong.,Xu, Zhijian.,Shen, Jingshan.,...&Zhu, Weiliang.(2021).One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-cis glycosylamines bearing various protected groups.ORGANIC & BIOMOLECULAR CHEMISTRY,19(7),1580-1588.
MLA Dong, Sanfeng,et al."One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-cis glycosylamines bearing various protected groups".ORGANIC & BIOMOLECULAR CHEMISTRY 19.7(2021):1580-1588.

入库方式： OAI收割

来源：上海药物研究所

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