Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates
文献类型：期刊论文
| 作者 | Zhu YG(朱玉根); Yu B(俞飚) |
| 刊名 | Chem.-Eur. J.
 |
| 出版日期 | 2015 |
| 卷号 | 21期号:24页码:8771-8780 |
| 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 |
| 通讯作者 | 俞飚 |
| 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. |
| 学科主题 | 生命有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1002/chem.201500648 |
| 语种 | 英语 |
| WOS记录号 | WOS:000355287000020 |
| 源URL | [http://ir.sioc.ac.cn/handle/331003/39504]  |
| 专题 | 上海有机化学研究所_生命有机化学国家重点实验室 |
| 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 |
| 推荐引用方式 GB/T 7714 | 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. |
| APA | 朱玉根,&俞飚.(2015).Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates.Chem.-Eur. J.,21(24),8771-8780. |
| MLA | 朱玉根,et al."Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates".Chem.-Eur. J. 21.24(2015):8771-8780. |
入库方式： OAI收割
来源：上海有机化学研究所
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