Unusual Orthogonality in the Cleavage Process of Closely Related Chelating Protecting Groups for Carboxylic Acids by Using Different Metal Ions

Stephan Mundinger; Uwe Jakob; Willi Bannwarth

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Unusual Orthogonality in the Cleavage Process of Closely Related Chelating Protecting Groups for Carboxylic Acids by Using Different Metal Ions

机译：使用不同金属离子的羧酸紧密相关螯合保护基团裂解过程中的不寻常正交性

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Three structurally related relay protecting groups for carboxylic acids that are based on chelating amines have been developed. These protecting groups can easily be introduced by coupling the carboxylic acid and the corresponding amine in the presence of 2-(1Hbenzotriazole- 1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU). In addition to being stable to a whole array of reaction conditions, these protecting groups are also stable under acidic and basic conditions, allowing them to be used in combination with the ester protection of carboxylic acids. The cleavage of these protecting groups is activated by the chelation of metal ions, involving an unusual coordination of the amide nitrogen. Despite their similarity, cleavage of these protecting groups is possible in both a stepwise and an orthogonal fashion by applying different metal salts.

机译：已经开发了基于螯合胺的三个结构上相关的羧酸中继保护基。这些保护基可以通过在2-（1H苯并三唑-1-基）-1,1,3,3-四甲基脲四氟硼酸酯（TBTU）的存在下偶联羧酸和相应的胺来轻松引入。这些保护基除了对整个反应条件稳定外，在酸性和碱性条件下也稳定，因此可以与羧酸的酯保护结合使用。这些保护基的裂解被金属离子的螯合激活，这涉及酰胺氮的异常配位。尽管它们相似，但是通过施加不同的金属盐，可以逐步和正交方式裂解这些保护基。

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《Chemistry: A European journal》 |2014年第5期|共5页
作者
Stephan Mundinger; Uwe Jakob; Willi Bannwarth;
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正文语种 eng
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关键词
amides; protecting groups; carboxylic acids; orthogonality; chelators;

机译：酰胺;保护基;羧酸;正交性;螯合剂;

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1. Unusual Orthogonality in the Cleavage Process of Closely Related Chelating Protecting Groups for Carboxylic Acids by Using Different Metal Ions [J] . Stephan Mundinger, Uwe Jakob, Willi Bannwarth Chemistry: A European journal . 2014,第5期

机译：使用不同金属离子的羧酸紧密相关螯合保护基团裂解过程中的不寻常正交性
2. Chelating Carboxylic Acid Amides as Robust Relay Protecting Groups of Carboxylic Acids and their Cleavage under Mild Conditions [J] . Manuel C. Brohmer, Stephan Mundinger, Stefan Brase Angewandte Chemie . 2011,第27期

机译：螯合羧酸酰胺作为稳健的羧酸继电保护基团及其在温和条件下的裂解
3. A Metal-Organic Framework Containing Unusual Eight-Connected Zr-Oxo Secondary Building Units and Orthogonal Carboxylic Acids for Ultra-sensitive Metal Detection [J] . Carboni Michael, Lin Zekai, Abney Carter W., Chemistry: A European journal . 2014,第46期

机译：金属有机框架包含异常的八连接Zr-Oxo二级建筑单元和正交羧酸用于超灵敏金属检测
4. Mechanistic Insights on C-C Bond Cleavage, C-O Bond Cleavage, and Hydrogen Insertion in Light Carboxylic Acids Catalyzed by Dispersed Ruthenium Clusters in Aqueous Medium [C] . Junnan Shangguan, Ya-Huei (Cathy) Chin AIChE Annual Meeting . 2015

机译：在水性介质中分散的钌簇催化的光羧酸中C-C键切割，C-O键切割和氢气插入的机械洞察
5. I. Metal-ion interactions and transmembrane permeability of peroxynitrite. II. DNA binding and cleavage mechanisms of metal chelate-appended porphyrins. [D] . Marla, Sudhakar Shankar. 1997

机译：I.过氧亚硝酸盐的金属离子相互作用和跨膜渗透性。二。金属螯合物附加的卟啉的DNA结合和裂解机理。
6. A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-α-methylbenzyl-amino-5-carboxymethyl-cyclopentane-1-carboxylic acid [O] . Narciso M. Garrido, Mohamed M. El Hammoumi, David Díez, 2004

机译：正交功能化的2-N-苄基-N-α-甲基苄基-氨基-5-羧甲基-环戊烷-1-羧酸的不对称合成的新策略
7. A CONVENIENT PREPARATION OF AN ORTHOGONALLY PROTECTED Ca,Ca-DISUBSTITUTED AMINO ACID ANALOG OF LYSINE: 1-tert-BUTYLOXYCARBONYL-4-((9-FLUORENYLMETHYLOXYCARBONYL)AMINO)-PIPERIDINE-4-CARBOXYLIC ACID [O] . 2005

机译：方便制备正交保护的Ca，赖氨酸的Ca-二取代的氨基酸类似物：1-叔丁氧基羰基-4-（（9-芴基甲氧基羰基）氨基） - 哌啶-4-羧酸
8. Studies of Chelate Polymers. V. Chelate Polymers of Bis-Dithiocarbamic Acids and Metals [R] . Terent'ev, A. P., Rukhadze, E. G., Rode, V. V. 1964

机译：螯合聚合物的研究。 V.双二硫代氨基甲酸和金属的螯合聚合物

Unusual Orthogonality in the Cleavage Process of Closely Related Chelating Protecting Groups for Carboxylic Acids by Using Different Metal Ions

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