Stereoselective and Regioselective Preparation of C-Pentopyranosides and Formal Synthesis of Omarigliptin

doi:10.1002/ejoc.201601074

	Stereoselective and Regioselective Preparation of C-Pentopyranosides and Formal Synthesis of Omarigliptin
	Liu, Tongchao 1,2,3; Hou, Jian 4; Xie, Wuchen 2,3,5; Li, You 2,3,5; Ren, Huanming 2,3,5; Liang, Jianpeng 2,3; Xiong, Bing2,3 ; Chen, Guohua 5; Cheng, Maosheng 1; Zhao, Dongmei 1
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	2016-12
期号	34 页码:5624-5628
关键词	Asymmetric synthesis C-glycosides Drug design Epoxides Glycosylation
ISSN号	1434-193X
DOI	10.1002/ejoc.201601074
文献子类	Article
英文摘要	A readily available intermediate obtained from D-arabinose was identified as a versatile starting material for the stereoselective synthesis of C-pentopyranosides in one pot. For two of the C-pentopyranosides, subsequent epoxide ring formation and a regioselective opening process was proven to be a robust approach to 3-deoxy C-pentopyranosides in two to four steps. A key intermediate used in the preparation of omarigliptin was obtained in four steps. Most of the conversions were high-yielding and proceeded with high selectivities on a multigram scale.
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关键词	DIRECTED ENANTIOSELECTIVE SYNTHESIS ; ACTING DPP-4 INHIBITOR ; RING-OPENING REACTIONS ; FUNCTIONALIZED DIHYDROPYRANS ; NEODYSIHERBAINE-A ; ACID ; ARYLGLUCOSIDE ; NUCLEOPHILES ; ENANTIOMERS ; CONTRACTION
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000390760000005
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/275776]
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	Zhao, Dongmei; Shen, Jingkang; Chen, Yue-Lei
作者单位	1.Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, 103 Wenhua Lu, Shenyang 110016, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China; 4.Shanghai Shynedec Pharmaceut Co Ltd, 378 Jianlu Rd, Shanghai 200137, Peoples R China; 5.China Pharmaceut Univ, Sch Pharm, 24 Tongjiaxiang, Nanjing 210009, Jiangsu, Peoples R China
推荐引用方式 GB/T 7714	Liu, Tongchao,Hou, Jian,Xie, Wuchen,et al. Stereoselective and Regioselective Preparation of C-Pentopyranosides and Formal Synthesis of Omarigliptin[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2016(34):5624-5628.
APA	Liu, Tongchao.,Hou, Jian.,Xie, Wuchen.,Li, You.,Ren, Huanming.,...&Chen, Yue-Lei.(2016).Stereoselective and Regioselective Preparation of C-Pentopyranosides and Formal Synthesis of Omarigliptin.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(34),5624-5628.
MLA	Liu, Tongchao,et al."Stereoselective and Regioselective Preparation of C-Pentopyranosides and Formal Synthesis of Omarigliptin".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .34(2016):5624-5628.