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钯/聚三烯丙基胺溴化氢:一种用于6-氯嘌呤核糖核苷胺化反应及阿格列汀合成的高效水溶性催化体系。

Pd/PTABS: An Efficient Water-Soluble Catalytic System for the Amination of 6-Chloropurine Ribonucleoside and Synthesis of Alogliptin.

作者信息

Bhilare Shatrughn, Bandaru Siva Sankar Murthy, Kapdi Anant R, Sanghvi Yogesh S, Schulzke Carola

机构信息

Department of Chemistry, Institute of Chemical Technology, Mumbai, India.

Institut für Biochemie, Ernst-Moritz-Arndt-Universität Greifswald, Greifswald, Germany.

出版信息

Curr Protoc Nucleic Acid Chem. 2018 Sep;74(1):e58. doi: 10.1002/cpnc.58. Epub 2018 Aug 21.

DOI:10.1002/cpnc.58
PMID:30129702
Abstract

The synthesis and catalytic applications of the highly water-soluble ligand 7-phospha-1,3,5-triaza-admantane butane sultonate (PTABS) has been described. The synthesized PTABS ligand along with palladium acetate exhibits excellent reactivity towards the amination reaction of 6-chloro-9-(β-D-ribofuranosyl)-9H-purine at ambient temperature. This protocol offers an advantage over the previously published procedures for the amination of 6-chloropurine nucleoside furnishing 6-N-substituted adenosine analogues. The validation of the present strategy has been demonstrated via synthesis of a uracil-based, anti-diabetic drug alogliptin. © 2018 by John Wiley & Sons, Inc.

摘要

已描述了高水溶性配体7-磷杂-1,3,5-三氮杂金刚烷丁烷磺酸盐(PTABS)的合成及其催化应用。合成的PTABS配体与醋酸钯在室温下对6-氯-9-(β-D-呋喃核糖基)-9H-嘌呤的胺化反应表现出优异的反应活性。该方案相对于先前发表的用于6-氯嘌呤核苷胺化以提供6-N-取代腺苷类似物的方法具有优势。通过合成基于尿嘧啶的抗糖尿病药物阿格列汀证明了本策略的有效性。© 2018约翰威立父子公司。

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引用本文的文献

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Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes.高效钯催化剂的发现、合成和放大在核苷和杂芳烃修饰中的应用。
Molecules. 2020 Apr 3;25(7):1645. doi: 10.3390/molecules25071645.