Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 90866-33-4, is researched, SMILESS is O=C(OCC)C[C@@H](O)CCl, Molecular C6H11ClO3Journal, Cuihua Xuebao called Effective method for controlling the stereoselectivity in asymmetric reduction of β-oxo ester with yeast cells, Author is Yang, Zhonghua; Yao, Shanjing, the main research direction is oxoester asym reduction Saccharomyces enzyme inhibitor; stereoselective reduction oxoester Saccharomyces enzyme inhibitor.Quality Control of (R)-Ethyl 4-chloro-3-hydroxybutanoate.
Using the reduction of Et 4-chloro-3-oxobutanoate (COBE) to enantiomeric pure Et 4-chloro-3-hydroxybutanoate (CHBE) as the model reaction, the method for controlling the stereoselectivity of reduction of β-oxo esters by pretreatment of the yeast was studied. The primary technique was pretreatment of the yeast cells with enzyme inhibitors, such as allyl alc. and allyl bromide, for a period before asym. transformation of COBE. It was found that the stereoselectivity of the reduction reaction could be controlled to produce S-CHBE when the yeast cells were pretreated with allyl alc. The ee of S-CHBE was improved with increasing the concentration of allyl alc. and the pretreatment time. 95% for ee of S-CHBE could be reached when allyl alc. was 1 g/L and pretreatment time was 2 h. On the contrary, the pretreatment with allyl bromide could turn the stereoselectivity of this reduction reaction from S-CHBE to R-CHBE. Also the inhibitor concentration and pretreatment time had pos. effect on ee of R-CHBE. And the ee of R-CHBE could reach to 98 % when an appropriate condition was applied.
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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem