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Mechanistic Insight into the Conversion of Tetrose Sugars to Novel α‐Hydroxy Acid Platform Molecules
Author(s) -
Dusselier Michiel,
Van Wouwe Pieter,
de Clippel Filip,
Dijkmans Jan,
Gammon David W.,
Sels Bert F.
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200476
Subject(s) - biorefinery , chemistry , polyester , catalysis , molecule , lactic acid , organic chemistry , carbon fibers , biomass (ecology) , combinatorial chemistry , materials science , bacteria , raw material , biology , composite number , composite material , oceanography , geology , genetics
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.