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

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.