Suppr超能文献

C1-醇的直接脱水糖基化反应。

Direct Dehydrative Glycosylation of C1-Alcohols.

机构信息

Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO, 80309, USA.

出版信息

Chem Asian J. 2018 Oct 18;13(20):2978-2990. doi: 10.1002/asia.201800971. Epub 2018 Oct 1.

Abstract

Due to the central role played by carbohydrates in a multitude of biological processes, there has been a sustained interest in developing effective glycosylation methods to enable more thorough investigation of their essential functions. Among the myriad technologies available for stereoselective glycoside bond formation, dehydrative glycosylation possesses a distinct advantage given the unique properties of C1-alcohols such as straightforward preparation, stability, and a general reactivity compatible with a diverse set of reaction conditions. In this Focus Review, a survey of direct dehydrative glycosylations of C1-alcohols is provided with an emphasis on recent achievements, pervading limitations, mechanistic insights, and applications in total synthesis.

摘要

由于碳水化合物在多种生物过程中发挥着核心作用,因此人们一直致力于开发有效的糖基化方法,以更深入地研究其基本功能。在众多用于立体选择性糖苷键形成的技术中,脱水糖基化具有独特的优势,因为 C1-醇具有独特的性质,如制备简单、稳定性好以及与多种反应条件兼容的一般反应性。在这篇重点综述中,提供了 C1-醇的直接脱水糖基化反应的综述,重点介绍了最新的成就、普遍存在的局限性、反应机理和在全合成中的应用。

相似文献

1
Direct Dehydrative Glycosylation of C1-Alcohols.
Chem Asian J. 2018 Oct 18;13(20):2978-2990. doi: 10.1002/asia.201800971. Epub 2018 Oct 1.
2
Phenanthroline Catalysis in Stereoselective 1,2- Glycosylations.
Acc Chem Res. 2022 Dec 20;55(24):3738-3751. doi: 10.1021/acs.accounts.2c00636. Epub 2022 Nov 30.
4
Glycosyl Cross-Coupling of Anomeric Nucleophiles: Scope, Mechanism, and Applications in the Synthesis of Aryl C-Glycosides.
J Am Chem Soc. 2017 Dec 13;139(49):17908-17922. doi: 10.1021/jacs.7b08707. Epub 2017 Nov 30.
5
Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate.
Molecules. 2020 Mar 2;25(5):1103. doi: 10.3390/molecules25051103.
6
Brønsted Acid-Catalysed Dehydrative Substitution Reactions of Alcohols.
Chemistry. 2021 Jan 4;27(1):106-120. doi: 10.1002/chem.202002106. Epub 2020 Oct 15.
7
Chemoselective Iterative Dehydrative Glycosylation.
Angew Chem Int Ed Engl. 2001 Jan 19;40(2):414-417. doi: 10.1002/1521-3773(20010119)40:2<414::AID-ANIE414>3.0.CO;2-6.
8
Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.
J Am Chem Soc. 2020 Apr 15;142(15):7235-7242. doi: 10.1021/jacs.0c03165. Epub 2020 Apr 1.
10
Dehydrative glycosylation with cyclic phosphonium anhydrides.
Org Biomol Chem. 2016 Dec 20;15(1):51-55. doi: 10.1039/c6ob01812b.

引用本文的文献

1
Synthesis of New Glycometronidazole Compounds With Antifungal and Antifungal Biofilm Activity.
Chem Biol Drug Des. 2025 Aug;106(2):e70154. doi: 10.1111/cbdd.70154.
3
Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate.
Molecules. 2020 Mar 2;25(5):1103. doi: 10.3390/molecules25051103.

本文引用的文献

1
The Experimental Evidence in Support of Glycosylation Mechanisms at the S1-S2 Interface.
Chem Rev. 2018 Sep 12;118(17):8242-8284. doi: 10.1021/acs.chemrev.8b00083. Epub 2018 May 30.
2
Chemoselective Iterative Dehydrative Glycosylation.
Angew Chem Int Ed Engl. 2001 Jan 19;40(2):414-417. doi: 10.1002/1521-3773(20010119)40:2<414::AID-ANIE414>3.0.CO;2-6.
3
Direct Experimental Characterization of Glycosyl Cations by Infrared Ion Spectroscopy.
J Am Chem Soc. 2018 May 16;140(19):6034-6038. doi: 10.1021/jacs.8b01236. Epub 2018 May 7.
4
Constrained saccharides: a review of structure, biology, and synthesis.
Nat Prod Rep. 2018 Mar 1;35(3):220-229. doi: 10.1039/c7np00050b. Epub 2018 Mar 7.
5
Glycosyl Cross-Coupling of Anomeric Nucleophiles: Scope, Mechanism, and Applications in the Synthesis of Aryl C-Glycosides.
J Am Chem Soc. 2017 Dec 13;139(49):17908-17922. doi: 10.1021/jacs.7b08707. Epub 2017 Nov 30.
6
Glycans as Regulatory Elements of the Insulin/IGF System: Impact in Cancer Progression.
Int J Mol Sci. 2017 Sep 7;18(9):1921. doi: 10.3390/ijms18091921.
7
The influence of acceptor nucleophilicity on the glycosylation reaction mechanism.
Chem Sci. 2017 Mar 1;8(3):1867-1875. doi: 10.1039/c6sc04638j. Epub 2016 Nov 9.
8
N-glycan and Alzheimer's disease.
Biochim Biophys Acta Gen Subj. 2017 Oct;1861(10):2447-2454. doi: 10.1016/j.bbagen.2017.04.012. Epub 2017 Apr 29.
9
Dehydrative glycosylation with cyclic phosphonium anhydrides.
Org Biomol Chem. 2016 Dec 20;15(1):51-55. doi: 10.1039/c6ob01812b.
10
Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy- and 2,3,6-Trideoxy Sugars.
Angew Chem Int Ed Engl. 2016 Aug 16;55(34):10088-92. doi: 10.1002/anie.201605091. Epub 2016 Jul 19.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验