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Stereoselective Synthesis of the Trisaccharide Moiety of Ganglioside HLG-2
Xu, Fei-Fei; Wang, Yue; Xiong, De-Cai; Ye, Xin-Shan1
刊名JOURNAL OF ORGANIC CHEMISTRY
2014-01-17
DOI10.1021/jo402378a
79期:2页:797-802
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
资助者National Natural Science Foundation of China ; Ministry of Science and Technology of China ; National Natural Science Foundation of China ; Ministry of Science and Technology of China
研究领域[WOS]Chemistry
关键词[WOS]ALPHA-SELECTIVE SIALYLATIONS ; SIALIC-ACID ; O-SIALYLATION ; DONOR ; DICHLOROMETHANE ; THIOSIALOSIDE ; HOLOTHUROIDEA ; CONSTITUENTS ; SIALOSIDES ; EFFICIENT
英文摘要

The glycan portion of ganglioside HLG-2, which was identified in the extracts of the sea cucumber Holothuria leucospilota, was synthesized in a highly efficient and stereoselective manner. The unusual sequence of the trisaccharide moiety, alpha-N-glycolylsialy1-(2,4)-alpha-N-acetylsialyl-(2,6)-glucoside, was assembled by stereoselective coupling of a 5-N,4-O-carbonyl-protected sialyl phosphate donor, a N-2,2,2-trichloroethoxycarbonyl (Troc)-protected sialyl acceptor, and a (trimethylsily)ethyl-beta-glucosyl acceptor in high yield. The synthesis featured the high-yielding construction of two alpha-sialyl linkages.

语种英语
所属项目编号21232002 ; 21072014 ; 2012CB822100 ; 2013CB910700
资助者National Natural Science Foundation of China ; Ministry of Science and Technology of China ; National Natural Science Foundation of China ; Ministry of Science and Technology of China
WOS记录号WOS:000330099000034
Citation statistics
Cited Times:8[WOS]   [WOS Record]     [Related Records in WOS]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/65256
Collection北京大学药学院
作者单位1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
Recommended Citation
GB/T 7714
Xu, Fei-Fei,Wang, Yue,Xiong, De-Cai,et al. Stereoselective Synthesis of the Trisaccharide Moiety of Ganglioside HLG-2[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(2):797-802.
APA Xu, Fei-Fei,Wang, Yue,Xiong, De-Cai,&Ye, Xin-Shan.(2014).Stereoselective Synthesis of the Trisaccharide Moiety of Ganglioside HLG-2.JOURNAL OF ORGANIC CHEMISTRY,79(2),797-802.
MLA Xu, Fei-Fei,et al."Stereoselective Synthesis of the Trisaccharide Moiety of Ganglioside HLG-2".JOURNAL OF ORGANIC CHEMISTRY 79.2(2014):797-802.
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