Synthesis of ss-(1 -> 2)-Linked 6-Deoxy-L-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor

doi:10.1021/acs.joc.7b00057

	Synthesis of ss-(1 -> 2)-Linked 6-Deoxy-L-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor
	Shen, Zhengnan1,2 ; Mobarak, Hani 3; Li, Wei 2; Widmalm, Goran 3; Yu, Biao 2
	2017-03-17
发表期刊	JOURNAL OF ORGANIC CHEMISTRY (IF:3.3[JCR-2023],3.2[5-Year])
ISSN	0022-3263
卷号	82 期号:6 页码:3062-3071
发表状态	已发表
DOI	10.1021/acs.joc.7b00057
摘要	The ss-(1 -> 2)-linked 6-deoxy-L-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica 0:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-L-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh3AuNTf2. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation.
收录类别	SCI ; IC ; EI
语种	英语
资助项目	Swedish Research Council[20134859]
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000397077500026
出版者	AMER CHEMICAL SOC
EI入藏号	20171203475053
EI主题词	Glycosylation
EI分类号	Biology:461.9 ; Chemical Reactions:802.2
WOS关键词	BETA-L-RHAMNOPYRANOSIDES ; ANOMERIC METHYL GLYCOSIDES ; YERSINIA-ENTEROCOLITICA ; ORTHO-ALKYNYLBENZOATES ; CANDIDA-ALBICANS ; PROTECTING GROUP ; STEREOSELECTIVE-SYNTHESIS ; BACTERIAL PATHOGENS ; STRUCTURAL-ANALYSIS ; NMR-SPECTROSCOPY
原始文献类型	Article
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/1466
专题	物质科学与技术学院物质科学与技术学院_博士生
通讯作者	Widmalm, Goran; Yu, Biao
作者单位	1.ShanghaiTech Univ, Sch Phys Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China 3.Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden
第一作者单位	物质科学与技术学院
第一作者的第一单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Shen, Zhengnan,Mobarak, Hani,Li, Wei,et al. Synthesis of ss-(1 -> 2)-Linked 6-Deoxy-L-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(6):3062-3071.
APA	Shen, Zhengnan,Mobarak, Hani,Li, Wei,Widmalm, Goran,&Yu, Biao.(2017).Synthesis of ss-(1 -> 2)-Linked 6-Deoxy-L-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor.JOURNAL OF ORGANIC CHEMISTRY,82(6),3062-3071.
MLA	Shen, Zhengnan,et al."Synthesis of ss-(1 -> 2)-Linked 6-Deoxy-L-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor".JOURNAL OF ORGANIC CHEMISTRY 82.6(2017):3062-3071.