• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

基于构象限制策略的β-C-糖苷的高效合成：路易斯酸促进的端基异构位置的硅烷还原反应，具有完全的立体选择性。

An efficient synthesis of beta-C-glycosides based on the conformational restriction strategy: Lewis acid promoted silane reduction of the anomeric position with complete stereoselectivity.

作者信息

Terauchi Masaru, Abe Hiroshi, Matsuda Akira, Shuto Satoshi

机构信息

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

出版信息

Org Lett. 2004 Oct 14;6(21):3751-4. doi: 10.1021/ol048525+.

DOI:10.1021/ol048525+
PMID:15469340
Abstract

[reaction: see text] The reduction of glyconolactols having an anomeric carbon substituent by Et(3)SiH/TMSOTf proceeded with complete stereoselectivity to produce the corresponding beta-C-glycosides when the substrates were conformationally restricted in the (4)C(1)-chair form by a 3,4-O-cyclic diketal or a 4,6-O-benzylidene protecting group. Thus, the efficient construction of beta-C-glycosides was achieved on the basis of the conformation restriction strategy.

摘要

[反应：见正文] 当底物通过3,4-O-环状二酮或4,6-O-亚苄基保护基团以（4）C（1）-椅式构象受到限制时，用Et(3)SiH/TMSOTf还原具有异头碳取代基的糖醛醇，能以完全的立体选择性生成相应的β-C-糖苷。因此，基于构象限制策略实现了β-C-糖苷的高效构建。

相似文献

1
An efficient synthesis of beta-C-glycosides based on the conformational restriction strategy: Lewis acid promoted silane reduction of the anomeric position with complete stereoselectivity.基于构象限制策略的β-C-糖苷的高效合成：路易斯酸促进的端基异构位置的硅烷还原反应，具有完全的立体选择性。
Org Lett. 2004 Oct 14;6(21):3751-4. doi: 10.1021/ol048525+.
2
Control of alpha/beta stereoselectivity in Lewis acid promoted C-glycosidations using a controlling anomeric effect based on the conformational restriction strategy.基于构象限制策略，利用可控端基异构效应来控制路易斯酸促进的C-糖苷化反应中的α/β立体选择性。
Angew Chem Int Ed Engl. 2003 Mar 3;42(9):1021-3. doi: 10.1002/anie.200390261.
3
A study on the conformation-anomeric effect-stereoselectivity relationship in anomeric radical reactions, using conformationally restricted glucose derivatives as substrates.一项以构象受限的葡萄糖衍生物为底物，对端基自由基反应中的构象-端基异构效应-立体选择性关系进行的研究。
J Org Chem. 2003 Sep 19;68(19):7439-47. doi: 10.1021/jo030128+.
4
Synthesis of silylallene glycosides and diene diglycosides by C-glycosidation of D-glucal with 1,4-bis(trimethylsilyl)-2-butyne.通过D-葡糖醛与1,4-双（三甲基硅基）-2-丁炔的C-糖苷化反应合成甲硅烷基丙二烯糖苷和二烯二糖苷。
Org Lett. 2005 Apr 14;7(8):1585-8. doi: 10.1021/ol050265o.
5
Synthesis of ketopyranosyl glycosides and determination of their anomeric configuration on the basis of the three-bond carbon-proton couplings.基于三键碳-质子偶合的酮吡喃糖基糖苷的合成及其端基构型的测定。
Carbohydr Res. 2007 Aug 13;342(11):1393-404. doi: 10.1016/j.carres.2007.05.006. Epub 2007 May 18.
6
Stereodirected synthesis of aryl alpha-C-glycosides from 2-O-arylsilyl-glucopyranosides.由2-O-芳基硅基吡喃葡萄糖苷立体定向合成芳基α-C-糖苷。
Org Lett. 2003 Oct 2;5(20):3763-6. doi: 10.1021/ol035529q.
7
SnCl(4)- and TiCl(4)-catalyzed anomerization of acylated O- and S-glycosides: analysis of factors that lead to higher α:β anomer ratios and reaction rates.SnCl(4)- 和 TiCl(4)-催化的酰化 O- 和 S-糖苷的端基异构化：导致更高的 α:β 端基异构体比例和反应速率的因素分析。
J Org Chem. 2010 Oct 15;75(20):6747-55. doi: 10.1021/jo101090f.
8
Highly alpha- and beta-selective radical C-glycosylation reactions using a controlling anomeric effect based on the conformational restriction strategy. A study on the conformation-anomeric effect-stereoselectivity relationship in anomeric radical reactions.基于构象限制策略利用可控端基异构效应的高度α-和β-选择性自由基C-糖基化反应。端基自由基反应中构象-端基异构效应-立体选择性关系的研究。
J Am Chem Soc. 2001 Dec 5;123(48):11870-82. doi: 10.1021/ja011321t.
9
A systematic study of C-glucoside trisphosphates as myo-inositol trisphosphate receptor ligands. Synthesis of beta-C-glucoside trisphosphates based on the conformational restriction strategy.作为肌醇三磷酸受体配体的C-葡萄糖苷三磷酸酯的系统研究。基于构象限制策略合成β-C-葡萄糖苷三磷酸酯。
J Med Chem. 2006 Mar 23;49(6):1900-9. doi: 10.1021/jm051039n.
10
Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: stereoselective synthesis of glycosyl amides.糖基叠氮化物与三芳基膦的无痕施陶丁格连接：糖基酰胺的立体选择性合成
J Org Chem. 2006 Jun 9;71(12):4565-77. doi: 10.1021/jo060409s.

引用本文的文献

1
Second-Generation Total Synthesis of Prorocentin.普罗罗辛的第二代全合成。
Org Lett. 2023 Jul 7;25(26):4903-4907. doi: 10.1021/acs.orglett.3c01720. Epub 2023 Jun 26.
2
An iodoetherification-dehydroiodination strategy for the synthesis of complex spiroketals from dihydroxyalkene precursors.一种由二羟基烯烃前体合成复杂螺环缩酮的碘代醚化-脱碘化氢策略。
Org Biomol Chem. 2008 Apr 7;6(7):1165-9. doi: 10.1039/b719247a. Epub 2008 Feb 22.