Solleder Susanne C, Martens Steven, Espeel Pieter, Du Prez Filip, Meier Michael A R
Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Straße am Forum 7, 76131, Karlsruhe, Germany.
Polymer Chemistry Research Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4bis, 9000, Ghent, Belgium.
Chemistry. 2017 Oct 9;23(56):13906-13909. doi: 10.1002/chem.201703877. Epub 2017 Sep 8.
The straightforward convergent synthesis of sequence-defined and multifunctionalized macromolecules is described herein. The first combination of two efficient approaches for the synthesis of sequence-defined macromolecules is reported: thiolactone chemistry and the Passerini three-component reaction (P-3CR). The thiolactone moiety was used as protecting group for the thiol, allowing the synthesis of a library of sequence-defined α,ω-functionalized building blocks. These building blocks were subsequently efficiently coupled to oligomers with carboxylic acid functionalities in a P-3CR. Thus, larger oligomers with molecular weights of up to 4629.73 g mol were obtained in gram quantities in a convergent approach along with the introduction of independently selectable side chains (up to 15), thus clearly demonstrating the high versatility and the efficiency of the reported approach.
本文描述了序列定义且多功能化大分子的直接收敛合成。报道了两种用于合成序列定义大分子的有效方法的首次结合：硫内酯化学和帕瑟里尼三组分反应（P-3CR）。硫内酯部分用作硫醇的保护基团，从而能够合成一系列序列定义的α,ω-官能化结构单元。随后，这些结构单元在P-3CR中与具有羧酸官能团的低聚物高效偶联。因此，通过收敛方法以克级量获得了分子量高达4629.73 g/mol的更大低聚物，同时引入了可独立选择的侧链（最多15个），从而清楚地证明了所报道方法的高度通用性和效率。
