铁催化糖烯-氨基酰氧基化反应合成2-氨基糖
Iron-Catalyzed Glycal -Aminoacyloxylation for 2-Amino Saccharide Synthesis.
作者信息
Yin Le, Zhang Dakang, Jiang Zixiang, Wang Pinzhi, Levine Joseph C, Labbe Dylan L, Xu Hao
机构信息
Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453, United States.
出版信息
Tetrahedron Lett. 2025 Aug 30;167. doi: 10.1016/j.tetlet.2025.155678. Epub 2025 May 28.
Abstract
We report here a new catalytic and exclusively 1,2--selective glycal aminoacyloxylation method for 2-amino saccharide synthesis. This iron-catalyzed glycosylation is effective for a wide variety of glycosyl donors with consistently high stereoselectivity and excellent functional-group compatibility, which facilitates late-stage amino group incorporation for complex-carbohydrate synthesis.
摘要
我们在此报告一种用于合成2-氨基糖的新型催化且专一的1,2-选择性糖基氨基酰氧基化方法。这种铁催化的糖基化反应对多种糖基供体均有效，具有始终如一的高立体选择性和出色的官能团兼容性，这有利于在复杂碳水化合物合成的后期引入氨基。
相似文献
1
Iron-Catalyzed Glycal -Aminoacyloxylation for 2-Amino Saccharide Synthesis.铁催化糖烯-氨基酰氧基化反应合成2-氨基糖
Tetrahedron Lett. 2025 Aug 30;167. doi: 10.1016/j.tetlet.2025.155678. Epub 2025 May 28.
2
Stereoselective Multigram-Scale Tn Antigen Synthesis via the Iron-Catalyzed Glycal 1,2--Aminoglycosylation.通过铁催化的糖基1,2-氨基糖基化实现立体选择性多克级Tn抗原合成
Org Lett. 2025 May 30;27(21):5515-5520. doi: 10.1021/acs.orglett.5c01560. Epub 2025 May 16.
3
Stereoselective Glycosylation for 1,2--Aminoglycoside Assembly by Cooperative Atom Transfer Catalysis.通过协同原子转移催化实现1,2-氨基糖苷组装的立体选择性糖基化反应
J Am Chem Soc. 2024 Dec 11;146(49):33316-33323. doi: 10.1021/jacs.4c15084. Epub 2024 Nov 25.
4
Glycosyl Cross-Coupling of Anomeric Nucleophiles: Scope, Mechanism, and Applications in the Synthesis of Aryl C-Glycosides.糖基交叉偶联反应：反应范围、反应机理及其在芳基 C-糖苷合成中的应用。
J Am Chem Soc. 2017 Dec 13;139(49):17908-17922. doi: 10.1021/jacs.7b08707. Epub 2017 Nov 30.
5
Studies on the selectivity between nickel-catalyzed 1,2-cis-2-amino glycosylation of hydroxyl groups of thioglycoside acceptors with C2-substituted benzylidene N-phenyl trifluoroacetimidates and intermolecular aglycon transfer of the sulfide group.关于镍催化的 C2-取代苯亚甲基 N-苯基三氟乙酰亚胺基硫代糖苷受体上的羟基 1,2-顺式-2-氨基糖苷化选择性与硫代糖苷配基的分子间糖苷转移的研究。
J Org Chem. 2012 Sep 7;77(17):7330-43. doi: 10.1021/jo301050q. Epub 2012 Aug 9.
6
o-Cyanobenzoate: A Recyclable and Reusable Stereo-directing Group for β-O-Glycosylation via Pd(0)-catalyzed Ferrier Rearrangement.邻氰基苯甲酸酯：一种通过 Pd(0)催化的 Ferrier 重排实现β-O-糖苷化的可回收、可重复使用的立体定向基团。
Chem Asian J. 2022 Feb 1;17(3):e202101156. doi: 10.1002/asia.202101156. Epub 2021 Dec 30.
7
Palladium(II)-catalyzed rearrangement of glycal trichloroacetimidates: application to the stereoselective synthesis of glycosyl ureas.钯（II）催化的糖基三氯乙酰亚胺酯重排反应：在糖基脲立体选择性合成中的应用
J Am Chem Soc. 2008 Aug 20;130(33):11210-8. doi: 10.1021/ja803378k. Epub 2008 Jul 19.
8
Tunable stereoselectivity in the synthesis of α- and β-aryl glycosides using 1,2-α-anhydrosugars as glycosyl donors.使用1,2-α-脱水糖作为糖基供体合成α-和β-芳基糖苷时的可调立体选择性。
Carbohydr Res. 2017 Sep 8;449:95-102. doi: 10.1016/j.carres.2017.07.007. Epub 2017 Jul 25.
9
Nickel-catalyzed stereoselective glycosylation with C(2)-N-substituted benzylidene D-glucosamine and galactosamine trichloroacetimidates for the formation of 1,2-cis-2-amino glycosides. Applications to the synthesis of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GalNAc.镍催化的 C(2)-N-取代苯亚甲基 D-葡萄糖胺和半乳糖胺三氯乙酰亚氨酸酯的立体选择性糖基化反应，用于形成 1,2-顺式-2-氨基糖苷。在肝素二糖、GPI 锚定假二糖和α-GalNAc 的合成中的应用。
J Am Chem Soc. 2010 Oct 13;132(40):14288-302. doi: 10.1021/ja106682m.
10
General Strategy for Stereoselective Synthesis of β- N-Glycosyl Sulfonamides via Palladium-Catalyzed Glycosylation.通过钯催化的糖苷化反应构建β-N-糖基磺酰胺的立体选择性合成的一般策略。
Org Lett. 2018 Jul 6;20(13):3923-3927. doi: 10.1021/acs.orglett.8b01506. Epub 2018 Jun 19.
引用本文的文献
1
Iron-Catalyzed Stereoselective Nitrogen Atom Transfer for 1,2--Selective Glycosylation.铁催化的立体选择性氮原子转移用于1,2-选择性糖基化反应
Synlett. 2025 Aug 20. doi: 10.1055/a-2654-5609.
本文引用的文献
1
Stereoselective Multigram-Scale Tn Antigen Synthesis via the Iron-Catalyzed Glycal 1,2--Aminoglycosylation.通过铁催化的糖基1,2-氨基糖基化实现立体选择性多克级Tn抗原合成
Org Lett. 2025 May 30;27(21):5515-5520. doi: 10.1021/acs.orglett.5c01560. Epub 2025 May 16.
2
Stereoselective Glycosylation for 1,2--Aminoglycoside Assembly by Cooperative Atom Transfer Catalysis.通过协同原子转移催化实现1,2-氨基糖苷组装的立体选择性糖基化反应
J Am Chem Soc. 2024 Dec 11;146(49):33316-33323. doi: 10.1021/jacs.4c15084. Epub 2024 Nov 25.
3
Synthesis of 2-Amino-2-deoxy Sugars via Boron-Catalyzed Coupling of Glycosyl Fluorides and Silyl Ether Acceptors.通过硼催化糖基氟化物与硅醚受体的偶联反应合成2-氨基-2-脱氧糖
Org Lett. 2024 Sep 6;26(35):7474-7478. doi: 10.1021/acs.orglett.4c02888. Epub 2024 Aug 26.
4
Highly Stereoselective Synthesis of 2-Azido-2-Deoxyglycosides via Gold-Catalyzed S2 Glycosylation.通过金催化的S2糖基化反应高立体选择性合成2-叠氮基-2-脱氧糖苷
CCS Chem. 2023 Dec;5(12):2799-2807. doi: 10.31635/ccschem.023.202303086. Epub 2023 Dec 4.
5
Mechanistic Studies of Iron-PyBOX-Catalyzed Olefin Amino-Oxygenation with Functionalized Hydroxylamines.铁-吡咯并[2,3-b]吡啶-氧化合物催化功能化羟胺对烯烃进行氨基氧化反应的机理研究
Organometallics. 2023 Apr 28;42(14):1810-1817. doi: 10.1021/acs.organomet.3c00067. eCollection 2023 Jul 24.
6
Strategies in Synthesis of Heparin/Heparan Sulfate Oligosaccharides: 2000-Present.肝素/硫酸乙酰肝素寡糖的合成策略：2000 年至今。
Adv Carbohydr Chem Biochem. 2021;80:121-164. doi: 10.1016/bs.accb.2021.11.003.
7
Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals.氮中心自由基介导的糖醛的级联氨糖苷化反应。
Org Lett. 2021 Feb 19;23(4):1222-1227. doi: 10.1021/acs.orglett.0c04178. Epub 2021 Feb 9.
8
Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides.用于构建结构明确的Pel寡糖的试剂控制糖基化反应
J Org Chem. 2020 Dec 18;85(24):15872-15884. doi: 10.1021/acs.joc.0c00703. Epub 2020 May 18.
9
Chemoenzymatic Methods for the Synthesis of Glycoproteins.糖蛋白的化学酶法合成。
Chem Rev. 2018 Sep 12;118(17):8359-8413. doi: 10.1021/acs.chemrev.8b00238. Epub 2018 Aug 24.
10
Catalytic Glycosylations in Oligosaccharide Synthesis.寡糖合成中的催化糖基化反应。
Chem Rev. 2018 Sep 12;118(17):8285-8358. doi: 10.1021/acs.chemrev.8b00144. Epub 2018 Jul 3.
Zotero 插件