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Highly Stereoselective Nucleophilic Addition of Difluoromethyl-2-pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2-Ketoses

文献类型：期刊论文

作者Liu, Xiao1,2; Yin, Qiang1,2; Yin, Jian3; Chen, Guohua2; Wang, Xin1; You, Qi-Dong2; Chen, Yue-Lei1; Xiong, Bing1; Shen, Jingkang1
刊名EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
出版日期2014-10
期号28页码:6150-6154
关键词Nucleophilic addition Ketoses C-Glycosides Lactones Stereoselectivity
ISSN号1434-193X
DOI10.1002/ejoc.201402757
文献子类Article
英文摘要Nucleophilic addition of difluoromethyl-2-pyridyl sulfone to sugar lactones proceeded with good yield and excellent stereoselectivity. The hitherto unknown direct addition intermediates are stable and capable of useful conversions: Formal elimination of the anomeric hydroxy and sulfonyl groups yielded a 1-deoxy-1-difluoromethylene mannopyranose derivative. Directly from sugar lactones, by nucleophilic addition and subsequent one-pot reduction with allylmagnesium chloride, unprecedented fluorinated 2-ketose analogues were prepared efficiently.
WOS关键词GLUCOSAMINE PROPANE-1,3-DIYL DITHIOACETAL ; C-GLYCOSIDES ; CARBONYL-COMPOUNDS ; DERIVATIVES ; CARBASUGARS ; MANNOHEPTULOSE ; GLYCOSYLATION ; FUNCTIONALITY ; PHOSPHONATES ; REPLACEMENT
资助项目National Natural Science Foundation of China[81102306] ; National Natural Science Foundation of China[21302068] ; National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program", China[2012ZX09301001] ; National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program", China[2014ZX09507-002]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000342842500005
出版者WILEY-V C H VERLAG GMBH
源URL[http://119.78.100.183/handle/2S10ELR8/276884]  
专题药物化学研究室
通讯作者You, Qi-Dong
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China;
2.China Pharmaceut Univ, Sch Pharm, Nanjing 210009, Jiangsu, Peoples R China;
3.Jiangnan Univ, Key Lab Carbohydrate Chem & Biotechnol, Minist Educ, Sch Biotechnol, Wuxi 214122, Peoples R China
推荐引用方式
GB/T 7714		 Liu, Xiao,Yin, Qiang,Yin, Jian,et al. Highly Stereoselective Nucleophilic Addition of Difluoromethyl-2-pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2-Ketoses[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2014(28):6150-6154.
APA Liu, Xiao.,Yin, Qiang.,Yin, Jian.,Chen, Guohua.,Wang, Xin.,...&Shen, Jingkang.(2014).Highly Stereoselective Nucleophilic Addition of Difluoromethyl-2-pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2-Ketoses.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(28),6150-6154.
MLA Liu, Xiao,et al."Highly Stereoselective Nucleophilic Addition of Difluoromethyl-2-pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2-Ketoses".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .28(2014):6150-6154.

入库方式： OAI收割

来源：上海药物研究所

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