• 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

通过易位反应获得基于单环亚氨基环糖醇的治疗剂。

Metathesis access to monocyclic iminocyclitol-based therapeutic agents.

机构信息

Institute of Organic Chemistry, Romanian Academy, 202B Spl. Independentei, P.O. Box 35-108, Bucharest 060023, Romania.

出版信息

Beilstein J Org Chem. 2011;7:699-716. doi: 10.3762/bjoc.7.81. Epub 2011 May 27.

DOI:10.3762/bjoc.7.81
PMID:21804866
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3135129/
Abstract

By focusing on recent developments on natural and non-natural azasugars (iminocyclitols), this review bolsters the case for the role of olefin metathesis reactions (RCM, CM) as key transformations in the multistep syntheses of pyrrolidine-, piperidine- and azepane-based iminocyclitols, as important therapeutic agents against a range of common diseases and as tools for studying metabolic disorders. Considerable improvements brought about by introduction of one or more metathesis steps are outlined, with emphasis on the exquisite steric control and atom-economical outcome of the overall process. The comparative performance of several established metathesis catalysts is also highlighted.

摘要

本文聚焦于天然和非天然氮杂环戊烷（亚氨基环戊醇）的最新进展，强调了烯烃复分解反应（RCM、CM）作为多步合成吡咯烷、哌啶和氮杂环庚烷基亚氨基环戊醇的关键转化，这些亚氨基环戊醇是治疗多种常见疾病的重要治疗剂，也是研究代谢紊乱的工具。本文概述了通过引入一个或多个复分解步骤带来的显著改进，重点介绍了整个过程的精确空间控制和原子经济性结果。还强调了几种已建立的复分解催化剂的比较性能。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/98a23bc2fc76/Beilstein_J_Org_Chem-07-699-g030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/35e8d331a58b/Beilstein_J_Org_Chem-07-699-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/04591690ce1f/Beilstein_J_Org_Chem-07-699-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/da863a954da6/Beilstein_J_Org_Chem-07-699-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/c5a0a60c6f84/Beilstein_J_Org_Chem-07-699-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/7db8433d8418/Beilstein_J_Org_Chem-07-699-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/fab1cea4a3e2/Beilstein_J_Org_Chem-07-699-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/3405f91d9d1e/Beilstein_J_Org_Chem-07-699-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/814dbd21f068/Beilstein_J_Org_Chem-07-699-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/c2fc9bece6b4/Beilstein_J_Org_Chem-07-699-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/00fc4c5f625f/Beilstein_J_Org_Chem-07-699-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/f59f204456a6/Beilstein_J_Org_Chem-07-699-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/c30e2b230756/Beilstein_J_Org_Chem-07-699-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/199fb4599bff/Beilstein_J_Org_Chem-07-699-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/dca17200906b/Beilstein_J_Org_Chem-07-699-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/2b140237c2fe/Beilstein_J_Org_Chem-07-699-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/9746ee69a9d5/Beilstein_J_Org_Chem-07-699-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/8632274df5bd/Beilstein_J_Org_Chem-07-699-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/425bd4e1072b/Beilstein_J_Org_Chem-07-699-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/d76e27d9aafe/Beilstein_J_Org_Chem-07-699-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/d697d16bf038/Beilstein_J_Org_Chem-07-699-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/2aa58801fa5c/Beilstein_J_Org_Chem-07-699-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/98a23bc2fc76/Beilstein_J_Org_Chem-07-699-g030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/35e8d331a58b/Beilstein_J_Org_Chem-07-699-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/04591690ce1f/Beilstein_J_Org_Chem-07-699-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/da863a954da6/Beilstein_J_Org_Chem-07-699-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/c5a0a60c6f84/Beilstein_J_Org_Chem-07-699-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/7db8433d8418/Beilstein_J_Org_Chem-07-699-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/fab1cea4a3e2/Beilstein_J_Org_Chem-07-699-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/3405f91d9d1e/Beilstein_J_Org_Chem-07-699-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/814dbd21f068/Beilstein_J_Org_Chem-07-699-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/c2fc9bece6b4/Beilstein_J_Org_Chem-07-699-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/00fc4c5f625f/Beilstein_J_Org_Chem-07-699-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/f59f204456a6/Beilstein_J_Org_Chem-07-699-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/c30e2b230756/Beilstein_J_Org_Chem-07-699-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/199fb4599bff/Beilstein_J_Org_Chem-07-699-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/dca17200906b/Beilstein_J_Org_Chem-07-699-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/2b140237c2fe/Beilstein_J_Org_Chem-07-699-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/9746ee69a9d5/Beilstein_J_Org_Chem-07-699-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/8632274df5bd/Beilstein_J_Org_Chem-07-699-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/425bd4e1072b/Beilstein_J_Org_Chem-07-699-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/d76e27d9aafe/Beilstein_J_Org_Chem-07-699-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/d697d16bf038/Beilstein_J_Org_Chem-07-699-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/2aa58801fa5c/Beilstein_J_Org_Chem-07-699-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5919/3135129/98a23bc2fc76/Beilstein_J_Org_Chem-07-699-g030.jpg

相似文献

1
Metathesis access to monocyclic iminocyclitol-based therapeutic agents.通过易位反应获得基于单环亚氨基环糖醇的治疗剂。
Beilstein J Org Chem. 2011;7:699-716. doi: 10.3762/bjoc.7.81. Epub 2011 May 27.
2
Recent developments in olefin cross-metathesis.烯烃交叉复分解反应的最新进展
Angew Chem Int Ed Engl. 2003 Apr 29;42(17):1900-23. doi: 10.1002/anie.200200556.
3
Tandem Catalysis Utilizing Olefin Metathesis Reactions.利用烯烃复分解反应的串联催化
Chemistry. 2016 Jul 4;22(28):9440-54. doi: 10.1002/chem.201505136. Epub 2016 May 20.
4
Microwave-assisted Olefin Metathesis as Pivotal Step in the Synthesis of Bioactive Compounds.微波辅助烯烃复分解反应作为生物活性化合物合成中的关键步骤。
Curr Med Chem. 2017;24(41):4538-4578. doi: 10.2174/0929867324666170314122820.
5
Taking Olefin Metathesis to the Limit: Stereocontrolled Synthesis of Trisubstituted Alkenes.将烯烃复分解反应发挥到极致：三取代烯烃的立体控制合成
Acc Chem Res. 2023 Sep 19;56(18):2426-2446. doi: 10.1021/acs.accounts.3c00341. Epub 2023 Aug 29.
6
ESIMS studies and calculations on alkali-metal adduct ions of ruthenium olefin metathesis catalysts and their catalytic activity in metathesis reactions.钌烯烃复分解催化剂的碱金属加合物离子的电喷雾电离质谱（ESIMS）研究与计算及其在复分解反应中的催化活性
Chemistry. 2009 Oct 19;15(41):10948-59. doi: 10.1002/chem.200900565.
7
Ligand Substitution of Ru -Alkylidenes to Ru(bpy) : Sequential Olefin Metathesis/Photoredox Catalysis.钌-亚烷基与钌（联吡啶）的配体取代：顺序烯烃复分解/光氧化还原催化
Chemistry. 2020 Feb 6;26(8):1772-1775. doi: 10.1002/chem.201905694. Epub 2020 Jan 23.
8
Bulky N-Phosphino-Functionalized N-Heterocyclic Carbene Ligands: Synthesis, Ruthenium Coordination Chemistry, and Ruthenium Alkylidene Complexes for Olefin Metathesis.大位阻N-膦基官能化N-杂环卡宾配体：合成、钌配位化学及用于烯烃复分解反应的钌亚烷基配合物
Inorg Chem. 2015 Nov 2;54(21):10126-40. doi: 10.1021/acs.inorgchem.5b00513. Epub 2015 Oct 19.
9
Alkane metathesis by tandem alkane-dehydrogenation-olefin-metathesis catalysis and related chemistry.通过串联烷烃脱氢-烯烃复分解催化反应及相关化学实现的烷烃复分解反应。
Acc Chem Res. 2012 Jun 19;45(6):947-58. doi: 10.1021/ar3000713. Epub 2012 May 15.
10
The catalytic performance of Ru-NHC alkylidene complexes: PCy₃versus pyridine as the dissociating ligand.钌-NHC 亚烷基配合物的催化性能：三(环己基)膦（PCy₃）与吡啶作为离去配体的对比。
Beilstein J Org Chem. 2010 Dec 15;6:1188-98. doi: 10.3762/bjoc.6.136.

引用本文的文献

1
Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules.将烯炔复分解反应与成熟的有机转化反应相结合：一种用于生物活性分子可持续合成的强大策略。
Beilstein J Org Chem. 2020 Apr 16;16:738-755. doi: 10.3762/bjoc.16.68. eCollection 2020.
2
Editorial of Special Issue Ruthenium Complex: The Expanding Chemistry of the Ruthenium Complexes.专题编辑：钌配合物：钌配合物不断扩展的化学性质
Molecules. 2015 Sep 18;20(9):17244-74. doi: 10.3390/molecules200917244.
3
Enantioselective synthesis of polyhydroxyindolizidinone and quinolizidinone derivatives from a common precursor.

本文引用的文献

1
The catalytic performance of Ru-NHC alkylidene complexes: PCy₃versus pyridine as the dissociating ligand.钌-NHC 亚烷基配合物的催化性能：三(环己基)膦（PCy₃）与吡啶作为离去配体的对比。
Beilstein J Org Chem. 2010 Dec 15;6:1188-98. doi: 10.3762/bjoc.6.136.
2
Synthesis of L-altro-1-deoxynojirimycin, D-allo-1-deoxynojirimycin, and D-galacto-1-deoxynojirimycin from a single chiral cyanohydrin.从单一手性氰醇合成 L-艾杜糖-1-去氧野尻霉素、D-allo-1-去氧野尻霉素和 D-半乳糖-1-去氧野尻霉素。
Org Lett. 2010 Sep 3;12(17):3957-9. doi: 10.1021/ol101556k.
3
Protecting-group-free synthesis of amines: synthesis of primary amines from aldehydes via reductive amination.
从一个共同的前体中对多羟基吲哚里西啶酮和喹诺里西啶酮衍生物进行对映选择性合成。
Beilstein J Org Chem. 2014 Dec 22;10:3104-10. doi: 10.3762/bjoc.10.327. eCollection 2014.
4
Reactivation of a Ruthenium-Based Olefin Metathesis Catalyst.基于钌的烯烃复分解催化剂的再活化
Organometallics. 2013 Jan 14;32(1):5-8. doi: 10.1021/om301042a. Epub 2012 Dec 21.
无保护基合成胺：通过还原胺化反应从醛合成伯胺。
J Org Chem. 2010 Aug 20;75(16):5470-7. doi: 10.1021/jo100004c.
4
Chemoselective olefin metathesis transformations mediated by ruthenium complexes.钌配合物介导的烯烃复分解化学选择性转化。
Chem Soc Rev. 2010 Aug;39(8):3305-16. doi: 10.1039/b912410c. Epub 2010 Jun 30.
5
Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.钌基杂环卡宾配位烯烃复分解催化剂。
Chem Rev. 2010 Mar 10;110(3):1746-87. doi: 10.1021/cr9002424.
6
Convergent, stereoselective syntheses of the glycosidase inhibitors broussonetines D and M.糖苷酶抑制剂桑橙素D和M的汇聚式立体选择性合成。
Org Biomol Chem. 2009 Apr 7;7(7):1355-60. doi: 10.1039/b821431j. Epub 2009 Feb 9.
7
Novel mannosidase inhibitors probe glycoprotein degradation pathways in cells.新型甘露糖苷酶抑制剂探索细胞中糖蛋白的降解途径。
Glycoconj J. 2009 Dec;26(9):1109-16. doi: 10.1007/s10719-009-9231-3.
8
New building block for polyhydroxylated piperidine: total synthesis of 1,6-dideoxynojirimycin.
J Org Chem. 2008 Apr 4;73(7):2898-901. doi: 10.1021/jo702480y. Epub 2008 Mar 12.
9
New synthetic seven-membered 1-azasugars displaying potent inhibition towards glycosidases and glucosylceramide transferase.新型合成七元1-氮杂糖对糖苷酶和葡萄糖神经酰胺转移酶具有强效抑制作用。
Chembiochem. 2008 Jan 25;9(2):253-60. doi: 10.1002/cbic.200700496.
10
In an attempt to provide a user's guide to the galaxy of benzylidene, alkoxybenzylidene, and indenylidene ruthenium olefin metathesis catalysts.旨在为苄叉基、烷氧基苄叉基和茚基钌烯烃复分解催化剂的众多类型提供一份用户指南。
Chemistry. 2008;14(3):806-18. doi: 10.1002/chem.200701340.