Developing Cellulosic Waste Products as Platform Chemicals: Protecting Group Chemistry of α-Glucoisosaccharinic Acid

Michael Almond, Mustapha Suleiman Galadima, Matthew Hawkins, Daniel Winder, Thomas Robshaw, Megan Waddoups, Paul Humphreys, Andrew Laws

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.
Original languageEnglish
Pages (from-to)97-105
Number of pages9
JournalCarbohydrate Research
Volume455
Early online date26 Nov 2017
DOIs
Publication statusPublished - Jan 2018

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