Suppr超能文献

寡糖合成的反向正交策略。

Reverse orthogonal strategy for oligosaccharide synthesis.

机构信息

Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.

出版信息

Chem Commun (Camb). 2011 Oct 14;47(38):10602-4. doi: 10.1039/c1cc13409d. Epub 2011 Sep 5.

Abstract

Herein, we report the invention of a novel expeditious concept for oligosaccharide synthesis. Unlike the classic orthogonal strategy based on leaving groups, the reverse approach is based on orthogonal protecting groups, herein p-methoxybenzyl and 4-pentenoyl, which allows for efficient oligosaccharide assembly in the reverse direction.

摘要

在此,我们报告了一种新颖的寡糖合成策略。与基于离去基团的经典正交策略不同,该反方向策略基于正交保护基,即 p-甲氧基苄基和 4-戊烯酰基,这使得在反方向上能够有效地进行寡糖组装。

相似文献

1
Reverse orthogonal strategy for oligosaccharide synthesis.
Chem Commun (Camb). 2011 Oct 14;47(38):10602-4. doi: 10.1039/c1cc13409d. Epub 2011 Sep 5.
3
Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.
Carbohydr Res. 2011 Sep 6;346(12):1371-88. doi: 10.1016/j.carres.2011.05.004. Epub 2011 May 18.
4
Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis.
J Org Chem. 2022 Aug 5;87(15):9887-9895. doi: 10.1021/acs.joc.2c00905. Epub 2022 Jul 21.
6
Application of the superarmed glycosyl donor to chemoselective oligosaccharide synthesis.
Org Lett. 2008 Jun 5;10(11):2107-10. doi: 10.1021/ol800648d. Epub 2008 May 1.
8
Advances in Protecting Groups for Oligosaccharide Synthesis.
Chem Asian J. 2020 Feb 17;15(4):450-462. doi: 10.1002/asia.201901621. Epub 2020 Jan 23.
9
S-Benzimidazolyl glycosides as a platform for oligosaccharide synthesis by an active-latent strategy.
Angew Chem Int Ed Engl. 2011 Apr 26;50(18):4197-201. doi: 10.1002/anie.201007212. Epub 2011 Mar 23.

引用本文的文献

1
Enhanced experimental set-up for HPLC-based automated synthesis and purification of carbohydrate building blocks.
Carbohydr Res. 2025 Sep;555:109554. doi: 10.1016/j.carres.2025.109554. Epub 2025 May 27.
2
HPLC-Based Automated Synthesis and Purification of Carbohydrates.
Chemistry. 2024 Aug 1;30(43):e202401214. doi: 10.1002/chem.202401214. Epub 2024 May 29.
3
Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis.
J Org Chem. 2022 Aug 5;87(15):9887-9895. doi: 10.1021/acs.joc.2c00905. Epub 2022 Jul 21.
4
Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.
Chem Rev. 2018 Sep 12;118(17):8105-8150. doi: 10.1021/acs.chemrev.8b00051. Epub 2018 Jun 28.
5
Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation.
Org Lett. 2016 May 6;18(9):2316-9. doi: 10.1021/acs.orglett.6b01102. Epub 2016 Apr 26.
6
Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.
Chem Heterocycl Compd (N Y). 2012 Apr;48(1). doi: 10.1007/s10593-012-0984-4.
7
Regioselective monodeprotection of peracetylated carbohydrates.
Nat Protoc. 2012 Oct;7(10):1783-96. doi: 10.1038/nprot.2012.098. Epub 2012 Sep 6.

本文引用的文献

1
Discovery and design of carbohydrate-based therapeutics.
Expert Opin Drug Discov. 2010 Aug;5(8):721-37. doi: 10.1517/17460441.2010.497811. Epub 2010 Jun 17.
2
Ionic catch and release oligosaccharide synthesis (ICROS).
Chem Commun (Camb). 2011 Apr 21;47(15):4526-8. doi: 10.1039/c0cc05580h. Epub 2011 Mar 9.
3
Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters.
J Org Chem. 2009 Dec 4;74(23):9233-6. doi: 10.1021/jo901837z.
4
Recent progress in chemical and chemoenzymatic synthesis of carbohydrates.
Curr Opin Chem Biol. 2009 Dec;13(5-6):573-81. doi: 10.1016/j.cbpa.2009.09.013. Epub 2009 Oct 14.
6
Oligosaccharide synthesis: from conventional methods to modern expeditious strategies.
Adv Carbohydr Chem Biochem. 2009;62:161-250. doi: 10.1016/S0065-2318(09)00005-5.
8
STICS: surface-tethered iterative carbohydrate synthesis.
Chem Commun (Camb). 2009 Apr 14(14):1834-6. doi: 10.1039/b817684a. Epub 2009 Feb 18.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验