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

doi:10.1039/d0ob02477e

	One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-cis glycosylamines bearing various protected groups
	Dong, Sanfeng 1,2; Zhao, Yitian 1,2; Shi, Yulong 1,3; Xu, Zhijian 1,3; Shen, Jingshan 1,3; Jia, Qi 2; Li, Yiming 2; Chen, Kaixian 1,2,3; Li, Bo 1,3; Zhu, Weiliang 1,2,3
刊名	ORGANIC & BIOMOLECULAR CHEMISTRY
	2021-02-21
卷号	19 期号:7 页码:1580-1588
ISSN号	1477-0520
DOI	10.1039/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
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000621563000015
内容类型	期刊论文
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.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 2.Shanghai Univ Tradit Chinese Med, 1200 Cailun 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.