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

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.

GISA_protect_repository_2017Dec.pdf - Accepted Version

Download (540kB) | Preview


Downloads per month over past year

Add to AnyAdd to TwitterAdd to FacebookAdd to LinkedinAdd to PinterestAdd to Email