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Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol
Qin, Qi; Xiong, De-Cai; Ye, Xin-Shan
关键词Additive Stereoselectivity Glycosylation Preactivation Aryl glycoside
刊名CARBOHYDRATE RESEARCH
2015-02-11
DOI10.1016/j.carres.2014.07.004
403页:104-114
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biochemistry & Molecular Biology ; Chemistry, Applied ; Chemistry, Organic
研究领域[WOS]Biochemistry & Molecular Biology ; Chemistry
关键词[WOS]NEIGHBORING GROUP PARTICIPATION ; HEPARIN-LIKE OLIGOSACCHARIDES ; ONE-POT SYNTHESIS ; BETA-MANNOPYRANOSIDES ; O-GLCNAC ; GLYCOCINNASPERIMICIN-D ; GLYCOSIDIC LINKAGES ; ALPHA-GLYCOSYLATION ; ENDOCYCLIC CLEAVAGE ; SULFOXIDE METHOD
英文摘要

Stereo-controllable glycosylation reactions of 2,3-oxazolidinone protected glucosamine thioglycoside donor with different phenol acceptors based on preactivation protocol, are described. It was found that BF3.Et2O worked as alpha-directing additive, while TTBP acted as beta-directing additive. Simply by altering additives, either alpha-aryl glycosides or beta-aryl glycosides were achieved in a stereoselective manner. The additives were also applied to the stereoselective glycosylation reactions of 2,3-oxazolidinone protected galactosamine donor with phenol substrates. (C) 2014 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000349085900013
项目编号2012CB822100 ; 2013CB910700 ; 2012ZX09502001-001 ; 21232002 ; 2142015 ; YETP0063
资助机构Ministry of Science and Technology of China ; National Natural Science Foundation of China ; Beijing Natural Science Foundation ; Beijing Higher Education Young Elite Teacher Project
引用统计
被引频次:8[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/58410
专题北京大学药学院
北京大学药学院_天然药物与仿生药物国家重点实验室
北京大学药学院_药物化学系
作者单位Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Qin, Qi,Xiong, De-Cai,Ye, Xin-Shan. Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol[J]. CARBOHYDRATE RESEARCH,2015,403:104-114.
APA Qin, Qi,Xiong, De-Cai,&Ye, Xin-Shan.(2015).Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol.CARBOHYDRATE RESEARCH,403,104-114.
MLA Qin, Qi,et al."Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol".CARBOHYDRATE RESEARCH 403(2015):104-114.
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