Mechanistic Insight into the Conversion of Tetrose Sugars to Novel α‐Hydroxy Acid Platform Molecules
2012; Wiley; Volume: 5; Issue: 2 Linguagem: Inglês
10.1002/cctc.201200476
ISSN1867-3899
AutoresMichiel Dusselier, Pieter Van Wouwe, Filip de Clippel, Jan Dijkmans, David W. Gammon, Bert F. Sels,
Tópico(s)biodegradable polymer synthesis and properties
ResumoAbstract α‐Hydroxy acids (AHAs) such as lactic acid are considered platform molecules in the biorefinery concept and have high‐end applications in solvents and biodegradable polyester plastics. The synthesis of AHAs with a four‐carbon backbone structure is a recently emerging field. New biomass‐related routes towards their production could stimulate their practical use in new polyester plastics. Herein, we report the unique catalytic activity of soluble tin metal salts for converting tetroses, namely erythrulose and erythrose, into new four‐carbon‐backbone AHAs such as methyl vinylglycolate and methyl‐4‐methoxy‐2‐hydroxybutanoate. An in situ NMR study together with deuterium labeling experiments and control experiments with intermediates allowed us to propose a detailed reaction pathway.
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