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Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass

Sheppard, T; Hailes, H; Benhamou, L; Ward, D; Bucar, D-K; Lye, G; Foster, R; ... Sloan, L; + view all (2019) Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass. Green Chemistry , 21 (8) pp. 2035-2042. 10.1039/C9GC00448C. Green open access

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Abstract

Carbohydrate biomass represents a potentially valuable sustainable source of raw materials for chemical synthesis, but for many applications, selective deoxygenation/dehydration of the sugars present is necessary to access compounds with useful chemical and physical properties. Selective dehydration of pentose sugars to give tetrahydrofurans can be achieved by treatment of the corresponding N,N-dimethylhydrazones under acidic or basic conditions, with the two approaches showing complementary stereoselectivity. The dehydration process is readily scalable and the THF hydrazones derived from arabinose, ribose, xylose and rhamnose were converted into a range of useful fragments containing primary alcohol, ketone, carboxylic acid or amine functional groups. These compounds have potentially useful physiochemical properties making them suitable for incorporation into fragment/lead generation libraries for medicinal chemistry. It was also shown that L-arabinose hydrazone could be obtained selectively from a crude sample of hydrolysed sugar beet pulp.

Type: Article
Title: Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/C9GC00448C
Publisher version: https://doi.org/10.1039/c9gc00448c
Language: English
Additional information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. https://creativecommons.org/licenses/by/3.0/
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Biochemical Engineering
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10070509
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