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.
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。
相似文献
1
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.
J Org Chem. 2020 Dec 18;85(24):16196-16206. doi: 10.1021/acs.joc.0c02370. Epub 2020 Nov 17.
2
Synthesis of 2-Amino-2-deoxy-β-d-mannosides via Stereoselective Anomeric -Alkylation of 2,3-Oxazolidinone-Protected d-Mannosamine: Synthesis of the Trisaccharide Repeating Unit of 19F Polysaccharide.
Org Lett. 2023 Jun 9;25(22):4214-4218. doi: 10.1021/acs.orglett.3c01564. Epub 2023 May 31.
3
Synthesis of 2,3-diazido-2,3-dideoxy-β-d-mannosides and 2,3-diazido-2,3-dideoxy-β-d-mannuronic acid via stereoselective anomeric O-alkylation.
Carbohydr Res. 2024 Nov;545:109279. doi: 10.1016/j.carres.2024.109279. Epub 2024 Sep 21.
4
Stereoselective Synthesis of β-d-Manno-heptopyranoside via CsCO-Mediated Anomeric -Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Surface-Layer Glycoprotein.
J Org Chem. 2022 May 20;87(10):6588-6600. doi: 10.1021/acs.joc.2c00168. Epub 2022 May 10.
5
Mannosazide methyl uronate donors. Glycosylating properties and use in the construction of β-ManNAcA-containing oligosaccharides.
J Org Chem. 2010 Dec 3;75(23):7990-8002. doi: 10.1021/jo101779v. Epub 2010 Nov 4.
6
-Mannosylation via -Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans.
European J Org Chem. 2020 Apr 23;2020(15):2291-2301. doi: 10.1002/ejoc.202000313. Epub 2020 Mar 19.
7
Potassium carbonate-mediated -selective anomeric -alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids.
Tetrahedron Lett. 2023 Jun 6;122. doi: 10.1016/j.tetlet.2023.154511. Epub 2023 Apr 19.
8
Biosynthetic elongation of isolated teichuronic acid polymers via glucosyl- and N-acetylmannosaminuronosyltransferases from solubilized cytoplasmic membrane fragments of Micrococcus luteus.
J Bacteriol. 1990 Sep;172(9):5160-4. doi: 10.1128/jb.172.9.5160-5164.1990.
9
Direct synthesis of 2-deoxy-β-glycosides via anomeric O-alkylation with secondary electrophiles.
J Am Chem Soc. 2014 Feb 26;136(8):3172-5. doi: 10.1021/ja4116956. Epub 2014 Feb 11.
10
Synthesis of Kdo-alpha-glycosides of lipid A derivatives.
Carbohydr Res. 1993 Aug 17;246:137-59. doi: 10.1016/0008-6215(93)84029-6.
引用本文的文献
1
Synthesis of 2,3-diazido-2,3-dideoxy-β-d-mannosides and 2,3-diazido-2,3-dideoxy-β-d-mannuronic acid via stereoselective anomeric O-alkylation.
Carbohydr Res. 2024 Nov;545:109279. doi: 10.1016/j.carres.2024.109279. Epub 2024 Sep 21.
2
Synthesis of Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl -1,1-Dimethylpropargyl Carbamate Donors.
J Org Chem. 2024 Sep 6;89(17):12547-12558. doi: 10.1021/acs.joc.4c01484. Epub 2024 Aug 13.
3
Dynamic Kinetic Stereoselective Glycosylation via Rh and Chiral Phosphoric Acid-Cocatalyzed Carbenoid Insertion to the Anomeric OH Bond for the Synthesis of Glycoconjugates.
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.
Tetrahedron Lett. 2023 Jun 6;122. doi: 10.1016/j.tetlet.2023.154511. Epub 2023 Apr 19.
5
Synthesis of 2-Amino-2-deoxy-β-d-mannosides via Stereoselective Anomeric -Alkylation of 2,3-Oxazolidinone-Protected d-Mannosamine: Synthesis of the Trisaccharide Repeating Unit of 19F Polysaccharide.
Org Lett. 2023 Jun 9;25(22):4214-4218. doi: 10.1021/acs.orglett.3c01564. Epub 2023 May 31.
6
Stereoselective β-Mannosylation via Anomeric -Alkylation with L-Sugar-Derived Electrophiles.
European J Org Chem. 2021 Dec 28;2021(48):6682-6687. doi: 10.1002/ejoc.202100903. Epub 2021 Nov 12.
7
Stereoselective Synthesis of β-d-Manno-heptopyranoside via CsCO-Mediated Anomeric -Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Surface-Layer Glycoprotein.
J Org Chem. 2022 May 20;87(10):6588-6600. doi: 10.1021/acs.joc.2c00168. Epub 2022 May 10.
本文引用的文献
1
Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.
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.
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.
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.
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.
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.
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.
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.
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.
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.
J Am Chem Soc. 2012 Sep 19;134(37):15556-62. doi: 10.1021/ja3069962. Epub 2012 Sep 11.
Zotero 插件