83867-83-8Relevant academic research and scientific papers
A scalable chemoenzymatic preparation of (R)-tetrahydrofuran-2-carboxylic acid
Fujima, Yoshito,Hirayama, Yoshihiro,Ikunaka, Masaya,Nishimoto, Yukifumi
, p. 1385 - 1391 (2003)
To develop a practical scalable approach to (R)-tetrahydrofuran-2-carboxylic acid (THFC) 1, a chiral building block for furopenem 2, enantioselective hydrolysis of its esters is explored: When ethyl (±)-tetrahydrofuran-2-carboxylate 3d (2 M, 288 g/L) is digested by an Aspergillus melleus protease {0.2% (w/v)} in a 1.5 M potassium phosphate buffer (pH 8) for 20 h, enantioselective hydrolysis proceeds with E=60 to give (R)-THFC 1 in 94.4% ee. On separation from the left-over antipodal ester (S)-3d by partition, (R)-THFC 1 is treated with N,N-dicyclohexylamine (DCHA) in methyl ethyl ketone/methanol (5:1) to precipitate the crystalline salt 4 that contains (R)-THFC 1 of >99% ee in 22% overall yield from (±)-3d.
Preparation method of tetrahydrofuranacetic acid and ester compounds thereof
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Paragraph 0026, (2021/05/12)
The invention provides a preparation method of tetrahydrofuranacetic acid and ester compounds thereof. The preparation method comprises the following steps: in a proper solvent, in a reducing atmosphere and under the action of a hydrogenation catalyst, carrying out a reduction reaction on furanacetic acid and ester compounds thereof under the conditions that a pressure is 0.1-10MPa and a temperature is 30-250 DEG C for 0.1-72 hours, separating out the catalyst, and distilling out the solvent to obtain the target products, namely tetrahydrofuranacetic acid and the ester compounds thereof. Under relatively mild and environment-friendly conditions, efficient conversion of bio-based furanacetic acid and esters thereof is achieved, industrial production of the reaction is facilitated, platform molecules can be converted into various important intermediates or terminal products through chemical catalysis upgrading to replace existing petrochemical products, dependence on fossil resources is reduced, and the application range of biomass is expanded.
