Issue 31, 2024

Xylose-derived thionocarbamates as a synthetic handle towards a functional platform of sugar-based polymers

Abstract

The derivatisation of D-xylose with potassium thiocyanate is presented as a versatile synthetic handle towards functional synthetic carbohydrate polymers. The reactivity of the resulting 1,3-oxazolidine-2-thione (OZT) group with alkyl bromides is ubiquitous and, herein, has been exploited to synthesise seven bio-derived monomers with different pendant functionalities. These monomers were polymerised with dithiols to yield functional poly(ester-thioethers) with a broad spectrum of properties. From a single non-functionalised OZT-polymer, a variety of post-polymerisation modification approaches are possible to functionalise the materials with different pendant groups. These results present a novel simple methodology to tailor the properties of synthetic carbohydrate polymers to different applications.

Graphical abstract: Xylose-derived thionocarbamates as a synthetic handle towards a functional platform of sugar-based polymers

Supplementary files

Article information

Article type
Paper
Submitted
17 may 2024
Accepted
01 iyl 2024
First published
15 iyl 2024
This article is Open Access
Creative Commons BY license

Polym. Chem., 2024,15, 3149-3156

Xylose-derived thionocarbamates as a synthetic handle towards a functional platform of sugar-based polymers

J. R. Runge, B. Davies and A. Buchard, Polym. Chem., 2024, 15, 3149 DOI: 10.1039/D4PY00540F

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