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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Chem Rev. 2018 Sep 12;118(17):8285-8358. doi: 10.1021/acs.chemrev.8b00144. Epub 2018 Jul 3.
Zotero 插件