821783-49-7

Basic information

• Product Name: Butanoic acid, 2-(4-chlorophenoxy)-3-hydroxy-, ethyl ester, (2R,3S)-
• CAS NO: 821783-49-7
• Molecular Formula: C12H15ClO4
• Molecular Weight: 258.702
• Mol File: 821783-49-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 2-(4-chlorophenoxy)-3-hydroxy-, ethyl ester, (2R,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 2-(4-chlorophenoxy)-3-hydroxy-, ethyl ester, (2R,3S)-(821783-49-7)
• EPA Substance Registry System: Butanoic acid, 2-(4-chlorophenoxy)-3-hydroxy-, ethyl ester, (2R,3S)-(821783-49-7)

Safety Data

• Hazardous Substances Data: 821783-49-7(Hazardous Substances Data)

Upstream product

• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 119138-47-5 ethyl 2-(4-chlorophenoxy)-3-oxobutanoate 
• 110444-43-4 ethyl (2R,3S)-2-chloro-3-hydroxybutanoate 
• 110508-08-2 Ethyl (2S,3S)-2,3-epoxybutanoate 
• 106-48-9 4-chloro-phenol 

Relevant articles and documents

Stereoselective prostereogenic 3-oxo ester reduction mediated by a novel yeast alcohol dehydrogenase derived from Kluyveromyces marxianus CBS 6556

A yeast alcohol dehydrogenase (ADH) has been purified up to a purification factor value of 21,731-fold from Kluyveromyces marxianus CBS 6556. The purification procedure consisted of two chromatographic steps (DEAE-anion exchange and affinity chromatography). The optimal pH was 7, its optimal temperature was 40°C and its co-factor was NADPH. This novel ADH efficiently mediated the reduction of 3-oxo esters with a high degree of stereoselectivity, providing chiral alcohols having the (S) absolute configuration at the newly formed stereogenic centre by delivering the hydride from the re-face of the prochiral carbonyl compounds.

Diastereo- and enantioselective bioreduction of ethyl 2-(4-chlorophenoxy)- 3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts

Growing and resting cells of several yeasts, which catalyze the hydride transfer to a carbonyl, were screened and used in conditions to find out the suitable methodology to prepare clofibrate analogues. Clofibrate is an antilipidemic drug. In particular, the bioreduction of ethyl 2-(4-chlorophenoxy)-3-oxobutanoate 1 was investigated to separately prepare the four possible stereoisomers of the ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate 2. Compound (2R,3S)-2 was prepared with ee = 97% and 73% yield in the presence of Kluyveromyces marxianus; (2S,3S)-2 preparation with ee >99% in 9% and 33% yield was mediated by Saccharomyces cerevisiae CBS 7336 and Trigonopsis variabilis, respectively. Diastereomeric excess values of all the reactions investigated were up to >99%. Furthermore, enantiomeric excesses of the bioconversions varied between 2% and >99% using growing cells and, 12% and >99% using resting cells. The absolute configuration of (2R,3S)-2 was established by X-ray analysis of the corresponding acid 3.