Journal
GREEN CHEMISTRY
Volume 24, Issue 5, Pages 2000-2009Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc00186a
Keywords
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Funding
- National Key Research and Development Program of China [2019YFC1906603]
- National Natural Science Foundation of China [22078152]
- Jiangsu Synergetic Innovation Centre for Advanced Bio-Manufacture [XTC1806]
- Six Talent Peaks Project in Jiangsu Province [SWYY-030/SWYY-118]
- Key Project for Entrepreneurship Leader Talent of Suzhou [ZXL2019156]
- General Program of Shenzhen [JCYJ20190808155417018]
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This study developed a novel pathway for synthesizing the high-value pharmaceutical intermediate 2-furylglyoxylic acid from a bio-based sugar-acid monomer. Through experiments and theoretical calculations, the transformation process and the flexibility and versatility of furan-based compounds were explored.
We developed a novel pathway for preparing the high-value pharmaceutical intermediate 2-furylglyoxylic acid (2FGA) from 2-keto-l-gulonic acid (2KGA), a bio-based sugar-acid monomer and precursor of vitamin C, via dehydration. 100 g L-1 methyl 2-keto-l-gulonicate (Me-2KGA) was transformed into methyl 2-furylglyoxylicate (Me-2FGA) with a maximum yield of 79.4%, competing with the yields obtained via traditional commercial synthesis methods. Subsequently, characterisation methods and theoretical calculations were employed; it was confirmed that natural 2KGA, with a 2,5-cyclic configuration, was esterified initially, it then underwent a transformation to an opened intermediate which further recyclized in a 3,6-cyclic configuration via removing one molecule of water, and this was finally dehydrated to Me-2FGA. This study offers novel insight into the flexibility and versatility of furan-based compounds.
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