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学科主题: 生命有机化学
题名: Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates
其他题名: 1-alpha-glycosyloxy-isochromenylium-4-gold(I)中间体介导的高立体选择性的beta-甘露糖糖苷化
作者: Zhu YG(朱玉根); Yu B(俞飚)
通讯作者: 俞飚
刊名: Chem.-Eur. J.
发表日期: 2015
DOI: 10.1002/chem.201500648
卷: 21, 期:24, 页:8771-8780
收录类别: SCI
文章类型: 论文
英文摘要: While the gold(I)-catalyzed glycosylation reaction with 4,6-O-benzylidene tethered mannosyl ortho-alkynylbenzoates as donors falls squarely into the category of the Crich-type -selective mannosylation when Ph3PAuOTf is used as the catalyst, in that the mannosyl -triflates are invoked, replacement of the -OTf in the gold(I) complex with less nucleophilic counter anions (i.e., -NTf2, -SbF6, -BF4, and (-BAr4F)) leads to complete loss of -selectivity with the mannosyl ortho-alkynylbenzoate -donors. Nevertheless, with the -donors, the mannosylation reactions under the catalysis of Ph3PAuBAr4F (BAr4F=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) are especially highly -selective and accommodate a broad scope of substrates; these include glycosylation with mannosyl donors installed with a bulky TBS group at O3, donors bearing 4,6-di-O-benzoyl groups, and acceptors known as sterically unmatched or hindered. For the ortho-alkynylbenzoate -donors, an anomerization and glycosylation sequence can also ensure the highly -selective mannosylation. The 1--mannosyloxy-isochromenylium-4-gold(I) complex (C), readily generated upon activation of the -mannosyl ortho-alkynylbenzoate (1) with Ph3PAuBAr4F at -35 degrees C, was well characterized by NMR spectroscopy; the occurrence of this species accounts for the high -selectivity in the present mannosylation.
语种: 英语
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WOS记录号: WOS:000355287000020
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39504
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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作者单位: 中科院上海有机化学研究所, 生命有机化学国家重点实验室

Recommended Citation:
Zhu YG,Yu B. Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates[J]. Chem.-Eur. J.,2015,21(24):8771-8780.
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