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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

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.

作者信息

Bhetuwal Bishwa Raj, Wu Fenglang, Meng Shuai, 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.

出版信息

J Org Chem. 2020 Dec 18;85(24):16196-16206. doi: 10.1021/acs.joc.0c02370. Epub 2020 Nov 17.

DOI:10.1021/acs.joc.0c02370
PMID:33201716
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7799176/
Abstract

Cesium carbonate-mediated anomeric O-alkylation of various protected 2-azido-2-deoxy-d-mannoses with primary triflate electrophiles afforded corresponding 2-azido-2-deoxy-β-mannosides in good yields and excellent anomeric selectivity. In addition, 1,3-dibromo-5,5-dimethylhydantoin was found to be the optimal oxidant for preparation of those 2-azido-2-deoxy-d-mannoses from their corresponding thioglycosides. The utilization of this method was demonstrated in the synthesis of a tetrasaccharide fragment of teichuronic acid containing -acetyl-β-d-mannosaminuronic acid (ManNAcA).

摘要

碳酸铯介导的各种受保护的2-叠氮基-2-脱氧-D-甘露糖与伯三氟甲磺酸酯亲电试剂的端基O-烷基化反应，以良好的产率和优异的端基选择性得到了相应的2-叠氮基-2-脱氧-β-甘露糖苷。此外，发现1,3-二溴-5,5-二甲基海因是由相应的硫代糖苷制备这些2-叠氮基-2-脱氧-D-甘露糖的最佳氧化剂。该方法在含有N-乙酰基-β-D-甘露糖胺糖醛酸（ManNAcA）的磷壁酸四糖片段的合成中得到了应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/1e34898abdc3/nihms-1656720-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/462f0bf04923/nihms-1656720-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/b07dfa588b94/nihms-1656720-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/f063e82dea09/nihms-1656720-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/1e34898abdc3/nihms-1656720-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/462f0bf04923/nihms-1656720-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/b07dfa588b94/nihms-1656720-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/f063e82dea09/nihms-1656720-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7287/7799176/1e34898abdc3/nihms-1656720-f0005.jpg

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本文引用的文献

1
Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.通过溴介导的硫代糖苷氧化简便合成糖内酯
J Carbohydr Chem. 2019;38(2):109-126. doi: 10.1080/07328303.2019.1581889. Epub 2019 Mar 20.
2
4,6- O-Pyruvyl Ketal Modified N-Acetylmannosamine of the Secondary Cell Wall Polysaccharide of Bacillus anthracis Is the Anchoring Residue for Its Surface Layer Proteins.4,6-O- 吡喃乙酰基甘露糖基-N-乙酰基葡萄糖胺是炭疽杆菌次生细胞壁多糖的锚固残基，是其表面层蛋白的锚固残基。
J Am Chem Soc. 2018 Dec 12;140(49):17079-17085. doi: 10.1021/jacs.8b08857. Epub 2018 Nov 30.
3
Boronic-Acid-Catalyzed Regioselective and 1,2- cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via Si-Type Mechanism.
Dynamic Kinetic Stereoselective Glycosylation via Rh and Chiral Phosphoric Acid-Cocatalyzed Carbenoid Insertion to the Anomeric OH Bond for the Synthesis of Glycoconjugates.
通过铑和手性磷酸共催化类卡宾插入异头羟基键实现动态动力学立体选择性糖基化用于合成糖缀合物
Angew Chem Int Ed Engl. 2023 Sep 25;62(39):e202307144. doi: 10.1002/anie.202307144. Epub 2023 Aug 21.
4
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.
5
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Org Lett. 2023 Jun 9;25(22):4214-4218. doi: 10.1021/acs.orglett.3c01564. Epub 2023 May 31.
6
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European J Org Chem. 2021 Dec 28;2021(48):6682-6687. doi: 10.1002/ejoc.202100903. Epub 2021 Nov 12.
7
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J Org Chem. 2022 May 20;87(10):6588-6600. doi: 10.1021/acs.joc.2c00168. Epub 2022 May 10.
硼酸酸催化的通过 Si 型机理的非保护糖受体的区域选择性和 1,2-顺式立体选择性糖苷化反应。
J Am Chem Soc. 2018 Mar 14;140(10):3644-3651. doi: 10.1021/jacs.7b12108. Epub 2018 Feb 26.
4
Stereoselective Construction of β-Mannopyranosides by Anomeric O-Alkylation: Synthesis of the Trisaccharide Core of N-linked Glycans.通过端基 O-烷基化构建 β-甘露糖苷：N-连接聚糖三糖核心的合成。
Angew Chem Int Ed Engl. 2016 Apr 4;55(15):4767-71. doi: 10.1002/anie.201600488. Epub 2016 Mar 7.
5
Deciphering Antigenic Determinants of Streptococcus pneumoniae Serotype 4 Capsular Polysaccharide using Synthetic Oligosaccharides.使用合成寡糖解析肺炎链球菌4型荚膜多糖的抗原决定簇
ACS Chem Biol. 2016 Feb 19;11(2):335-44. doi: 10.1021/acschembio.5b00768. Epub 2016 Jan 4.
6
Chemical Synthesis Elucidates the Immunological Importance of a Pyruvate Modification in the Capsular Polysaccharide of Streptococcus pneumoniae Serotype 4.化学合成阐明了肺炎链球菌血清型 4 荚膜多糖中丙酮酸修饰的免疫学重要性。
Angew Chem Int Ed Engl. 2015 Aug 17;54(34):10016-9. doi: 10.1002/anie.201504847. Epub 2015 Jul 24.
7
Stereocontrolled 1,2- glycosylation as the driving force of progress in synthetic carbohydrate chemistry.立体控制的1,2-糖基化作为合成碳水化合物化学进展的驱动力。
Chem Sci. 2015 May 1;6(5):2687-2704. doi: 10.1039/C5SC00280J.
8
Synthesis of the Tetrasaccharide Repeating Unit from Acinetobacter baumannii Serogroup O18 Capitalizing on Phosphorus-Containing Leaving Groups.利用含磷离去基团合成鲍曼不动杆菌O18血清群的四糖重复单元
J Org Chem. 2015 May 1;80(9):4278-88. doi: 10.1021/acs.joc.5b00139. Epub 2015 Apr 15.
9
Synthesis of Staphylococcus aureus Type 5 trisaccharide repeating unit: solving the problem of lactamization.金黄色葡萄球菌5型三糖重复单元的合成：解决内酰胺化问题。
Org Lett. 2015 Feb 20;17(4):928-31. doi: 10.1021/acs.orglett.5b00031. Epub 2015 Feb 6.
10
Endolysins of Bacillus anthracis bacteriophages recognize unique carbohydrate epitopes of vegetative cell wall polysaccharides with high affinity and selectivity.炭疽杆菌噬菌体的内溶素以高亲和力和选择性识别营养细胞细胞壁多糖的独特碳水化合物表位。
J Am Chem Soc. 2012 Sep 19;134(37):15556-62. doi: 10.1021/ja3069962. Epub 2012 Sep 11.