Facile conversion of glycosyloxymethyl-furfural into gamma-keto-carboxylic acid building blocks towards a sustainable chemical industry

Brust, Andreas and Lichtenthaler, Frieder W. (2013) Facile conversion of glycosyloxymethyl-furfural into gamma-keto-carboxylic acid building blocks towards a sustainable chemical industry. Green Chemistry, 15 5: 1368-1372. doi:10.1039/c3gc40185e


Author Brust, Andreas
Lichtenthaler, Frieder W.
Title Facile conversion of glycosyloxymethyl-furfural into gamma-keto-carboxylic acid building blocks towards a sustainable chemical industry
Formatted title
Facile conversion of glycosyloxymethyl-furfural into γ-keto-carboxylic acid building blocks towards a sustainable chemical industry
Journal name Green Chemistry   Check publisher's open access policy
ISSN 1463-9262
1463-9270
Publication date 2013-01
Sub-type Article (original research)
DOI 10.1039/c3gc40185e
Open Access Status Not Open Access
Volume 15
Issue 5
Start page 1368
End page 1372
Total pages 5
Place of publication Cambridge, United Kingdom
Publisher R S C Publications
Collection year 2014
Language eng
Formatted abstract
Carbohydrates, as cheap mass-products, promise to be outstanding candidates as sustainable raw materials (F. W. Lichtenthaler and S. Peters, C. R. Chim., 2004, 7, 65–90). To achieve the goal of carbohydrate utilisation as industry raw materials, environmental low impact conversions from sugars to high value reactive intermediates are needed. Here we present the facile access to γ-keto-carboxylic acid building blocks from the sucrose-based glycosyloxymethyl-furfural (GMF). Employing an oxidative ring opening strategy under careful selection of reaction conditions, allows for high yield conversions of the furan aglycon into γ-keto-carboxylic acid moieties without alteration of the sugar moiety attached. The resulting glycosylated building blocks were converted into selected heterocyclic products of the pyridazinone and benzodiazepinone type to exemplify the synthetic potential of these building blocks. All synthetic manipulations employed low environmental impact solvents, reagents, oxidants and protecting group free conversions.
Keyword Raw-materials
Isomaltulose
Polysaccharides
Chemistry
Polymers
Fructose
Access
Sugars
Furans
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Part 46 of the series Sugar-Derived Building Blocks.

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
Institute for Molecular Bioscience - Publications
 
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