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Developing cellulosic waste products as platform chemicals: protecting group chemistry of α-glucoisosaccharinic acid

Almond, Michael, Suleiman, Mustapha G., Hawkins, Matthew, Winder, Daniel, Robshaw, Thomas, Waddoups, Megan, Humphreys, Paul and Laws, Andrew P. (2018) Developing cellulosic waste products as platform chemicals: protecting group chemistry of α-glucoisosaccharinic acid. Carbohydrate Research, 455. pp. 97-105. ISSN 0008-6215

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Abstract

Alpha and beta-glucoisosaccharinic acids ((2S,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid and (2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) which are produced when cellulosic materials are treated with aqueous alkali are potentially valuable platform chemicals. Their highly functionalised carbon skeleton, with fixed chirality at C-2 and C-4, makes them ideal starting materials for use in synthesis. In order to assess the potential of these saccharinic acids as platform chemicals we have explored the protecting group chemistry of the lactone form of alpha-glucoisosaccharinic acid (α-GISAL). We report here the use of single and multiple step reaction pathways leading to the regioselective protection of the three different hydroxyl groups of α-GISAL. We report strategies for protecting the three different hydroxyl groups individually or in pairs. We also report the synthesis of a range of tri-O-protected α-GISAL derivatives where a number of the products contain orthogonal protecting groups.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Sharon Beastall
Date Deposited: 14 Dec 2017 11:26
Last Modified: 14 Dec 2017 22:41
URI: http://eprints.hud.ac.uk/id/eprint/34085

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