56816-01-4Relevant articles and documents
THE PRODUCT OF BAKER'S YEAST REDUCTION OF ETHYL 2-CHLORO-3-OXOBUTANOATE AS A PRECURSOR OF THE 1-ETHOXYCARBONYL 2(S)-HYDROXYPROPYL RADICAL
Hamdani, Mourad,Jeso, Bernard De,Deleuze, Herve,Saux, Annie,Maillard, Bernard
, p. 1233 - 1236 (1993)
Baker's yeast treatment of ethyl 2-chloro-3-oxobutanoate 1, diethyl 2-acetylmalonate 2 and ethyl 2-cyano-3-oxobutanoate 3 was effected in order to obtain enantiomerically enriched compounds.In contrast to the reaction of 2 and 3, efficient diastereo- and enantioselective reduction of 1 provided ethyl 2(R)-chloro-3(S)-hydroxybutanoate.This product was used as precursor of the 1-ethoxycarbonyl-2(S)-hydroxypropyl radical and the diastereoselectivity of the addition of this intermediate to alkenes was studied.
Simple syntheses of (+)-orthosporin and (-)-semivioxanthin methyl ether+
Deshpande,Rai, Beena,Khan
, p. 7159 - 7162 (1996)
Simple syntheses of (+)-orthosporin(1) and (-)-semivioxanthin methyl ether (11) are described from (S)-ethyl-3-hydroxybutyrate (5) and orsellinic acid derivatives 3 and 4 respectively.
A SIMPLE SYNTHESIS OF (S)-(+)-SULCATOL, THE PHEROMONE OF GNATHOTRICHUS RETUSUS, EMPLOYING BAKER'S YEAST FOR ASYMMETRIC REDUCTION
Mori, Kenji
, p. 1341 - 1342 (1981)
Ethyl (S)-3-hydroxybutanoate of 87percent optical purity was obtained by the yeast reduction of ethyl acetoacetate and was converted into 85-87percent optically pure (S)-(+)-sulcatol (6-methyl-5-hepten-2-ol) by a 5-step sequence in 73percent overall yield.
The Use of Organic Solvent Systems in the Yeast Mediated Reduction of Ethyl Acetoacetate
Jayasinghe, Leonard Y.,Kodituwakku, Devika,Smallridge, Andrew J.,Trewhella, Maurie A.
, p. 2528 - 2531 (1994)
The reduction of ethyl acetoacetate to ethyl (S)-3-hydroxybutyrate, mediated by freeze-dried yeast, proceeds in good yield (53-58percent) and with high enantioselectivity (>96percentee) in a number of organic solvents; petroleum ether, diethyl ether, toluene, and carbon tetrachloride.A small amount of water (0.8 ml (g-yeast)-1) is required for the reaction to proceed.The water/yeast/substrate ratio and the solvent polarity have been found to significantly influence the reactivity of the system.The enantiomeric excess was determined by gas chromatography employing a chiral column.
SYNTHESIS OF 3-HYDROXYBUTYRYL 3-HYDROXYBUTYRATE AND RELATED COMPOUNDS
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Paragraph 0308; 0331-0333, (2021/04/02)
In various embodiments methods of preparing hydroxybutyryl 3-hydroxybutyrate and related compounds are provided along with methods of use thereof.
Effect of organic solvents on asymmetric reduction of β-keto esters using cyanobacterium Synechocystis sp. PCC 6803
Tanaka, Shusei,Kojima, Hideo,Takeda, Satomi,Yamanaka, Rio,Takemura, Tetsuo
supporting information, (2021/07/25)
The asymmetric reduction of tert-butyl 3-oxobutanoate by cyanobacterium Synechocystis sp. PCC 6803 under illumination with red LED light at 25 °C for 24 h afforded the corresponding (R)-β-hydroxy ester in 79% enantiomeric excess (ee) (81% yield), while the addition of toluene (1% (v/v)) to the system gave the corresponding (S)-β-hydroxy ester in >99% ee (87% yield). Organic solvents such as chloroform, benzene, ethylbenzene, cyclohexane, and methylcyclohexane showed similar effects and afforded the corresponding (S)-β-hydroxy ester in >99% ee. However, polar organic solvents, such as DMSO, THF, and ethanol, as well as dodecane—a hydrophobic solvent with a straight long-chain—did not exhibit such effects.