芳基氟代硫酸酯捕获的斯塔德格还原反应。
Aryl Fluorosulfate Trapped Staudinger Reduction.
机构信息
Department of Applied Chemistry, School of Food Science and Biotechnology, Zhejiang Gongshang University , Hangzhou 310035, China.
出版信息
Org Lett. 2017 Apr 7;19(7):1582-1585. doi: 10.1021/acs.orglett.7b00406. Epub 2017 Mar 23.
Abstract
A chemoselective Staudinger reduction/sulfur(VI) fluoride exchange cascade has been developed to join two chemical segments through an aryl sulfamate ester (RNH-SO-OAr) linkage. Aryl fluorosulfate is exploited in this work as the first tetrahedral electrophilic trap for the in situ generated iminophosphorane. Ten examples using azide-containing compounds are presented.
摘要
发展了一种通过芳基磺酰胺酯（RNH-SO-OAr）键连接两个化学片段的化学选择性Staudinger 还原/硫（VI）氟交换级联反应。本文利用芳基氟硫酸酯作为原位生成的亚磷酰胺的第一个四面体亲电陷阱。使用含叠氮化物的化合物展示了十个实例。
相似文献
1
Aryl Fluorosulfate Trapped Staudinger Reduction.芳基氟代硫酸酯捕获的斯塔德格还原反应。
Org Lett. 2017 Apr 7;19(7):1582-1585. doi: 10.1021/acs.orglett.7b00406. Epub 2017 Mar 23.
2
Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction.全氟芳基叠氮化物 Staudinger 反应：一种快速且生物正交的反应。
Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12117-12121. doi: 10.1002/anie.201705346. Epub 2017 Sep 1.
3
Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry.硫（六）氟化物交换（SuFEx）：点击化学的又一优秀反应。
Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9430-48. doi: 10.1002/anie.201309399. Epub 2014 Aug 11.
4
Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach.通过亚磷酰胺法合成磷酰氟化物和磷酰氟硫酯。
Org Biomol Chem. 2005 Mar 7;3(5):866-74. doi: 10.1039/b413552k. Epub 2005 Feb 1.
5
Chemoselective Tyrosine Bioconjugation through Sulfate Click Reaction.通过硫酸盐点击反应实现酪氨酸的化学选择性生物偶联。
Chemistry. 2018 Aug 1;24(43):10948-10952. doi: 10.1002/chem.201802380. Epub 2018 Jul 18.
6
Extension of a temperature-dependent aqueous solvation model to compounds containing nitrogen, fluorine, chlorine, bromine, and sulfur.将温度依赖性水合溶剂化模型扩展至含氮、氟、氯、溴和硫的化合物。
J Phys Chem B. 2008 Mar 13;112(10):3024-39. doi: 10.1021/jp076682v. Epub 2008 Feb 19.
7
Novel Approaches to Access Arylfluorosulfates and Sulfamoyl Fluorides Based on Sulfur (VI) Fluoride Exchange.基于六氟化硫交换获取芳基氟硫酸盐和氨磺酰氟的新方法。
Curr Protoc Chem Biol. 2019 Jun;11(2):e64. doi: 10.1002/cpch.64. Epub 2019 Feb 28.
8
Aryl trifluoroborates in Suzuki-Miyaura coupling: the roles of endogenous aryl boronic acid and fluoride.芳基三氟硼酸盐在铃木-宫浦偶联反应中的作用：内源性芳基硼酸和氟化物的作用
Angew Chem Int Ed Engl. 2010 Jul 12;49(30):5156-60. doi: 10.1002/anie.201001522.
9
-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides.膦芳基磺酰胺介导的芳基和烷基叠氮化物的 Staudinger 还原。
Molecules. 2022 Sep 5;27(17):5707. doi: 10.3390/molecules27175707.
10
New strategies for the synthesis of pyrimidine derivatives.嘧啶衍生物合成的新策略。
Chemistry. 2008;14(23):6836-44. doi: 10.1002/chem.200800014.
引用本文的文献
1
The Application of Bio-orthogonality for In Vivo Animal Imaging.生物正交性在体内动物成像中的应用。
Chem Biomed Imaging. 2023 Jul 7;1(5):434-447. doi: 10.1021/cbmi.3c00033. eCollection 2023 Aug 28.
2
Bioorthogonal chemistry.生物正交化学
Nat Rev Methods Primers. 2021;1. doi: 10.1038/s43586-021-00028-z. Epub 2021 Apr 15.
3
Developing bioorthogonal probes to span a spectrum of reactivities.开发一系列具有不同反应活性的生物正交探针。
Nat Rev Chem. 2020;4:476-489. doi: 10.1038/s41570-020-0205-0. Epub 2020 Jul 21.
4
Bioorthogonal Reactions of Triarylphosphines and Related Analogues.三芳基膦及其相关类似物的生物正交反应。
Chem Rev. 2021 Jun 23;121(12):6802-6849. doi: 10.1021/acs.chemrev.1c00014. Epub 2021 Jun 8.
5
SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase.SuFEx 使能的人中性粒细胞弹性蛋白酶共价抑制剂的无偏倚发现。
Proc Natl Acad Sci U S A. 2019 Sep 17;116(38):18808-18814. doi: 10.1073/pnas.1909972116. Epub 2019 Sep 4.
6
Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF )-Derived Connective Hubs for Bioconjugation to DNA and Proteins.生物相容的 SuFEx 点击化学：四氟化硫（SOF ）衍生的连接枢纽用于 DNA 和蛋白质的生物偶联。
Angew Chem Int Ed Engl. 2019 Jun 11;58(24):8029-8033. doi: 10.1002/anie.201902489. Epub 2019 May 8.
7
SuFEx Chemistry of Thionyl Tetrafluoride (SOF ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.亚硫酰四氟化物（SOF ）与有机锂亲核试剂的 SuFEx 化学：磺酰亚胺氟化物、亚砜亚胺、磺酰胺和磺酰亚氨基酯的合成。
Angew Chem Int Ed Engl. 2018 Feb 12;57(7):1939-1943. doi: 10.1002/anie.201712145. Epub 2018 Jan 16.
本文引用的文献
1
Reengineering Antibiotics to Combat Bacterial Resistance: Click Chemistry [1,2,3]-Triazole Vancomycin Dimers with Potent Activity against MRSA and VRE.重新设计抗生素以对抗细菌耐药性：点击化学法合成的[1,2,3]-三唑万古霉素二聚体对耐甲氧西林金黄色葡萄球菌（MRSA）和耐万古霉素肠球菌（VRE）具有强效活性 。
Chemistry. 2017 Jan 1;23(1):79-83. doi: 10.1002/chem.201604765. Epub 2016 Nov 11.
2
Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue.芳基氟硫酸酯通过与结合部位 Tyr 残基的化学选择性 SuFEx 反应使细胞内脂质结合蛋白失活。
J Am Chem Soc. 2016 Jun 15;138(23):7353-64. doi: 10.1021/jacs.6b02960. Epub 2016 Jun 2.
3
Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry.硫（六）氟化物交换（SuFEx）：点击化学的又一优秀反应。
Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9430-48. doi: 10.1002/anie.201309399. Epub 2014 Aug 11.
4
Leelamine mediates cancer cell death through inhibition of intracellular cholesterol transport.利拉明通过抑制细胞内胆固醇转运介导癌细胞死亡。
Mol Cancer Ther. 2014 Jul;13(7):1690-703. doi: 10.1158/1535-7163.MCT-13-0868. Epub 2014 Mar 31.
5
Targeting multiple key signaling pathways in melanoma using leelamine.使用利拉明靶向黑色素瘤中的多个关键信号通路。
Mol Cancer Ther. 2014 Jul;13(7):1679-89. doi: 10.1158/1535-7163.MCT-13-0867. Epub 2014 Mar 31.
6
Matrix-assisted polymer pen lithography induced Staudinger Ligation.基质辅助的聚合物笔刻蚀引发施陶丁格连接反应。
Chem Commun (Camb). 2012 May 21;48(41):4995-7. doi: 10.1039/c2cc31615c. Epub 2012 Apr 16.
7
Staudinger ligation as a method for bioconjugation.Staudinger 连接作为一种生物缀合方法。
Angew Chem Int Ed Engl. 2011 Sep 12;50(38):8806-27. doi: 10.1002/anie.201008102. Epub 2011 Sep 2.
8
Bioconjugation via azide-Staudinger ligation: an overview.通过叠氮化物-施陶丁格连接进行生物偶联：概述。
Chem Soc Rev. 2011 Sep;40(9):4840-71. doi: 10.1039/c0cs00123f. Epub 2011 Jun 17.
9
Towards quorum-quenching catalytic antibodies.迈向群体感应淬灭催化抗体。
Chem Commun (Camb). 2009 Feb 7(5):538-40. doi: 10.1039/b819819e. Epub 2008 Dec 11.
10
Mechanistic investigation of the staudinger ligation.施陶丁格连接反应的机理研究。
J Am Chem Soc. 2005 Mar 2;127(8):2686-95. doi: 10.1021/ja044461m.
Zotero 插件