135213-82-0Relevant academic research and scientific papers
5-(α-D-Glucoyloxymethyl)furfural: Preparation from Isomaltulose and Exploration of Its Ensuing Chemistry
Lichtenthaler, Frieder W.,Martin, Dierk,Weber, Thomas,Schiweck, Hubert
, p. 967 - 974 (2007/10/02)
An effective, practical, large-scale adaptable procedure has been developed to selectively dehydrate the fructose portion of isomaltulose 6)-fructose> (6): heating in DMSO in the presence of a strongly acidic ion-exchange resin generates α-D-glucosyloxymethylfurfural ("α-GMF", 3), isolable in yields up to 70percent.A variety of ensuing reactions have been exploited concerning the generation of products with industrial application profiles such as aldol-type additions to the dicyanovinyl (16), nitrovinyl (20), and benzoylvinyl (21) derivatives, or to the polymerizable unsubstituted vinyl compound (25) and the GMF-s acrylic acid (22).Oxidation to GMF-carboxylic acid (11) and reductive amination to GMF-amine 8 can be carried out without affecting the hydroxyl groups in the glucosyl portion; esterification of 11 with long-chain alcohols and N-acylation of 8 with fatty acid chlorides provide novel surfactants in which hydrophilic and hydrophobic parts of the molecule are separated by a heteroaromatic spacer. - Key Words: Furfural derivatives / Glycosides / Isomaltulose / Carbohydrates
