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

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.

Green is the new black – a review of technologies for carboxylic acid recovery from black liquor

“…One reason on the growing interest in these acids is their vast availability thus synthesis routes can then be developed allowing its use as starting material in synthetic chemistry. 69 In order to do so, it is necessary to develop also strategies to protect the different hydroxyl groups. 69 Other approach to employ these compounds is the use of the gluco-isosaccharinic acids as energy source for specific anaerobic bacteria that can effectively destroy chlorolignins.…”

“…69 In order to do so, it is necessary to develop also strategies to protect the different hydroxyl groups. 69 Other approach to employ these compounds is the use of the gluco-isosaccharinic acids as energy source for specific anaerobic bacteria that can effectively destroy chlorolignins. Thus, they could be applicable in the effluent treatment processes of the Kraft pulp mills.…”

Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity

“…It is pertinent to specify at this stage that some tin-catalyzed approaches in solution have appeared after the described report on the solvent-free conditions, with considerable simplification over the traditional stepwise stoichiometric method [48][49][50][51][52]. It is also worth observing that solvent-free benzylation protocols described herein have already been incorporated into a variety of synthetic projects [53][54][55][56], to testify their practical scope.…”

Sugarcane Bagasse Hydrolysis Enhancement by Microwave-Assisted Sulfolane Pretreatment

“…Further, during the pretreatment stage, other platform chemicals can be recovered [26]. For instance, saccharinic acids can be used for the preparation of various fine chemicals; as complexing agents for heavy metals [27], radionuclides and other materials; or as energy sources for aerobic and anaerobic bacteria [28].…”