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碳酸钾介导的与伯亲电试剂的α-选择性端基异构化烷基化反应：在鞘糖脂合成中的应用。

Potassium carbonate-mediated -selective anomeric -alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids.

作者信息

Lakshika Hettiarachchi Ishani, Wu Fenglang, Stoica Maria, Li Xiaohua, Zhu Jianglong

机构信息

Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States.

Department of Natural Sciences, University of Michigan-Dearborn, 4901 Evergreen Road, Dearborn, Michigan 48128, United States.

出版信息

Tetrahedron Lett. 2023 Jun 6;122. doi: 10.1016/j.tetlet.2023.154511. Epub 2023 Apr 19.

DOI:10.1016/j.tetlet.2023.154511
PMID:37334260
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10270675/
Abstract

Stereoselective construction of a variety of β-glycosides can be achieved using abundant and inexpensive KCO-mediated stereoselective anomeric O-alkylation of sugar lactols with primary electrophiles. In addition, application of this methodology to the synthesis of various azido-modified glycosphingolipids has been accomplished in good yields and excellent anomeric selectivity using sphingosine-derived primary triflate.

摘要

使用丰富且廉价的碳酸钾介导糖内脂与伯亲电试剂进行立体选择性异头碳O-烷基化反应，可实现多种β-糖苷的立体选择性构建。此外，利用源自鞘氨醇的伯三氟甲磺酸酯，已将该方法应用于各种叠氮基修饰的糖鞘脂的合成，产率良好且异头碳选择性优异。

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Potassium carbonate-mediated -selective anomeric -alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids.碳酸钾介导的与伯亲电试剂的α-选择性端基异构化烷基化反应：在鞘糖脂合成中的应用。
Tetrahedron Lett. 2023 Jun 6;122. doi: 10.1016/j.tetlet.2023.154511. Epub 2023 Apr 19.
2
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本文引用的文献

1
Stereoselective β-Mannosylation via Anomeric -Alkylation with L-Sugar-Derived Electrophiles.通过与L-糖衍生的亲电试剂进行端基烷基化实现立体选择性β-甘露糖基化反应。
European J Org Chem. 2021 Dec 28;2021(48):6682-6687. doi: 10.1002/ejoc.202100903. Epub 2021 Nov 12.
2
Ni(II)-Catalyzed Regio- and Stereoselective O-Alkylation for the Construction of 1,2--Glycosidic Linkages.镍(II)催化的区域和立体选择性 O-烷基化反应构建 1,2-糖苷键。
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3
Stereoselective Synthesis of β-d-Manno-heptopyranoside via CsCO-Mediated Anomeric -Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Surface-Layer Glycoprotein.通过 CsCO 介导的端基烯丙基烷基化反应立体选择性合成β-d-甘露庚糖苷：表面层糖蛋白四糖重复单元的合成。
J Org Chem. 2022 May 20;87(10):6588-6600. doi: 10.1021/acs.joc.2c00168. Epub 2022 May 10.
4
Stereoselective Synthesis of 2-Azido-2-deoxy-β-d-mannosides via CsCO-Mediated Anomeric O-Alkylation with Primary Triflates: Synthesis of a Tetrasaccharide Fragment of Teichuronic Acid.通过碳酸铯介导的端基 O-烷基化反应与伯三氟甲磺酸酯立体选择性合成 2-叠氮基-2-脱氧-β-D-甘露糖苷：磷壁酸四糖片段的合成
J Org Chem. 2020 Dec 18;85(24):16196-16206. doi: 10.1021/acs.joc.0c02370. Epub 2020 Nov 17.
5
-Mannosylation via -Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans.通过异头铯醇盐的β-烷基化进行甘露糖基化：复杂岩藻糖基化N-连接聚糖六糖核心的机理研究与合成
European J Org Chem. 2020 Apr 23;2020(15):2291-2301. doi: 10.1002/ejoc.202000313. Epub 2020 Mar 19.
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Org Lett. 2019 Feb 1;21(3):665-670. doi: 10.1021/acs.orglett.8b03823. Epub 2019 Jan 11.
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Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.自动化化学寡糖合成：传统挑战的新方法。
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A General Chemoenzymatic Strategy for the Synthesis of Glycosphingolipids.一种用于合成糖鞘脂的通用化学酶促策略。
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