Issue 39, 2022

Uniform soluble support for the large-scale synthesis of sequence-defined macromolecules

Abstract

Herein, a monodisperse soluble support is explored and used as an effective tool for the large-scale, liquid-phase synthesis of sequence-defined macromolecules. This support, based on a benzyl derivative with three long hydrophobic alkyl chains, combines the advantages of solid-phase and soluble support- based synthesis by allowing a straightforward workup after each coupling step and a direct characterisation of the intermediates, without prior cleavage from the support. While the soluble support is used for the multi-gram synthesis of thiolactone-based sequence-defined macromolecules, it can be applied for numerous other synthetic strategies too. Additionally, as it is uniform, it leads to a single peak in mass spectrometry and thus not to a molecular weight distribution as typically observed for standard polymeric soluble supports, thus facilitating the characterisation. To demonstrate the potential for the synthesis of sequence-defined macromolecules on a scale that is sufficient for their introduction in bulk material synthesis, a hexamer is prepared on a 14 g scale. Furthermore, two different cleavable linkers have been attached to the uniform soluble support, hence emphasizing the versatility of this strategy.

Graphical abstract: Uniform soluble support for the large-scale synthesis of sequence-defined macromolecules

Supplementary files

Article information

Article type
Paper
Submitted
07 Jul 2022
Accepted
06 Sep 2022
First published
10 Sep 2022

Polym. Chem., 2022,13, 5616-5624

Uniform soluble support for the large-scale synthesis of sequence-defined macromolecules

I. De Franceschi, C. Mertens, N. Badi and F. Du Prez, Polym. Chem., 2022, 13, 5616 DOI: 10.1039/D2PY00883A

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