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Synthesis of triazolyl-linked polysialic acids
Xiong, De-Cai; Zhou, Yichuan; Cui, Yuxin; Ye, Xin-Shan
关键词Polysialic Acid Click Reaction Triazole Cycloaddition Carbohydrate
刊名TETRAHEDRON
2014-12-09
DOI10.1016/j.tet.2014.10.028
70期:49页:9405-9412
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]STEREOSELECTIVE-SYNTHESIS ; NEISSERIA-MENINGITIDIS ; MENINGOCOCCAL POLYSACCHARIDES ; TRIMETHYLSILYL ACETYLENES ; CARBOHYDRATE-CHEMISTRY ; CHEMICAL PROPERTIES ; OLIGOSIALIC ACIDS ; TERMINAL ALKYNES ; CLICK REACTION ; SIALIC ACIDS
英文摘要

A new approach for the synthesis of triazolyl-linked alpha-(2-9) oligosialic acids by iterative copper(I)-catalyzed allcyne azide cycloaddition (CuAAC) and desilylation has been developed. By using propargyl alpha-sialoside 5 and trimethylsilylated-propargyl 9-azido-alpha-sialoside 3 as building blocks, triazolyl-linked alpha-(2-9) di- to octa-sialic acids were constructed in good to moderate yields. Finally, the pseudo-alpha-(2-9)-oligosialic acids were obtained very smoothly via O-deprotection. The oligosialic acids with a triazolyl-linkage represent a new type of pseudooligosialic acids. This protocol may find applications in the preparation of oligosialic acid analogues with biological importance. (C) 2014 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000345950800014
项目编号2012CB822100 ; 2012ZX09502001-001 ; 21102008 ; 21232002 ; YETP0063
资助机构Ministry of science and Technology of the People&prime ; s Republic of China ; National Natural Science Education of China ; Beijing Higher Education Young Elite Teacher Project
引用统计
被引频次:3[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/400002259/52329
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
Xiong, De-Cai,Zhou, Yichuan,Cui, Yuxin,et al. Synthesis of triazolyl-linked polysialic acids[J]. TETRAHEDRON,2014,70(49):9405-9412.
APA Xiong, De-Cai,Zhou, Yichuan,Cui, Yuxin,&Ye, Xin-Shan.(2014).Synthesis of triazolyl-linked polysialic acids.TETRAHEDRON,70(49),9405-9412.
MLA Xiong, De-Cai,et al."Synthesis of triazolyl-linked polysialic acids".TETRAHEDRON 70.49(2014):9405-9412.
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