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Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass

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 condiitions, 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

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Supplementary files

Publication details

The article was received on 04 Feb 2019, accepted on 13 Mar 2019 and first published on 14 Mar 2019


Article type: Paper
DOI: 10.1039/C9GC00448C
Citation: Green Chem., 2019, Accepted Manuscript

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    Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass

    L. Benhamou, R. W. Foster, D. P. Ward, K. Wheelhouse, L. Sloan, C. J. Tame, D. Bucar, G. J. Lye, H. Hailes and T. Sheppard, Green Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9GC00448C

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