In:
Green Chemistry, Royal Society of Chemistry (RSC), Vol. 24, No. 5 ( 2022), p. 2000-2009
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
1463-9262
,
1463-9270
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2022
detail.hit.zdb_id:
1485110-6
detail.hit.zdb_id:
2006274-6
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