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Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co-2(CO)(8)/Et3SiH/CO system
Zhao, Yue-tao; Niu, Shan; Huang, Lu-bai; Wang, Ji-ming; Yin, Zhao-jun; Li, Qing; Li, Zhong-jun
关键词Regioselective de-O-benzylation Dicobalt octacarbonyl Sucrose Raffinose family oligosaccharides Glycosylation
刊名TETRAHEDRON
2013-06-17
DOI10.1016/j.tet.2013.03.094
69期:24页:5022-5028
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
资助者National Basic Research Program of China (973 program) ; National Natural Science Foundation of China ; National Science &amp ; Technology Mega Project for Primary Drug Innovation from Ministry of Science and Technology of China ; National Basic Research Program of China (973 program) ; National Natural Science Foundation of China ; National Science &amp ; Technology Mega Project for Primary Drug Innovation from Ministry of Science and Technology of China
研究领域[WOS]Chemistry
关键词[WOS]CATALYZED-REACTIONS ; CARBON-MONOXIDE ; SUCROSE ; COBALT ; ETHERS ; CARBONYLATION ; DERIVATIZATION ; GLYCOSYLATION ; DEBENZYLATION ; CONSTITUENTS
英文摘要

A convenient approach for synthesis of raffinose, stachyose, and verbascose using sucrose as the starting material is presented. The key step is the regioselective de-O-benzylation with Co-2(CO)(8)/Et3SiH/CO system, followed by a high cc-selective glycosylation. The newly developed de-O-benzylation system is efficient in removing the primary benzyl groups of sucrose and raffinose under mild condition and with high selectivity. Using thioglycoside as donor, NIS/AgOTf as promoter and DTBMP as additive, glycosylation of acid labile sucrose substrate is achieved in high yield. (C) 2013 Elsevier Ltd. All rights reserved.

语种英语
所属项目编号2012CB822100 ; 20972012 ; 21072016 ; 2012ZX09502001-001
资助者National Basic Research Program of China (973 program) ; National Natural Science Foundation of China ; National Science &amp ; Technology Mega Project for Primary Drug Innovation from Ministry of Science and Technology of China ; National Basic Research Program of China (973 program) ; National Natural Science Foundation of China ; National Science &amp ; Technology Mega Project for Primary Drug Innovation from Ministry of Science and Technology of China
WOS记录号WOS:000319247000025
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/400002259/63048
专题北京大学药学院
作者单位Peking Univ, Hlth Sci Ctr, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs,Dept Chem Biol, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Zhao, Yue-tao,Niu, Shan,Huang, Lu-bai,et al. Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co-2(CO)(8)/Et3SiH/CO system[J]. TETRAHEDRON,2013,69(24):5022-5028.
APA Zhao, Yue-tao.,Niu, Shan.,Huang, Lu-bai.,Wang, Ji-ming.,Yin, Zhao-jun.,...&Li, Zhong-jun.(2013).Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co-2(CO)(8)/Et3SiH/CO system.TETRAHEDRON,69(24),5022-5028.
MLA Zhao, Yue-tao,et al."Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co-2(CO)(8)/Et3SiH/CO system".TETRAHEDRON 69.24(2013):5022-5028.
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