24621-61-2Relevant articles and documents
Synthesis of (R)-1,3-butanediol by enantioselective oxidation using whole recombinant Escherichia coli cells expressing (S)-specific secondary alcohol dehydrogenase
Yamamoto, Hiroaki,Matsuyama, Akinobu,Kobayashi, Yoshinori
, p. 925 - 927 (2002)
The synthesis of (R)-1,3-butanediol (BDO) from its racemate was studied using whole cells of recombinant Escherichia coli expressing an (S)-specific secondary alcohol dehydrogenase (CpSADH) from Candida parapsilosis by enantioselective oxidation. Under the optimized conditions, the yield of (R)-1,3-BDO reached 72.6 g/l, with a molar recovery yield of 48.4% from a racemate of 15% and an optical purity of 95% ee.
Diastereoselective route to (2R,5S)- and (2S,5S)-2-methyl-1,6-dioxaspiro[4.5]decane, a pheromone component of the wasp Paravespula vulgaris
Zarbin, Paulo H. G.,De Oliveira, Alfredo R. M.,Delay, Carlos E.
, p. 6849 - 6851 (2003)
A diastereoselective approach to (2R,5S)- and (2S,5S)-2-methyl-1,6-dioxaspiro[4.5]decane 1 and 1a is described. The route starts with an alkylation reaction among the cyclopentanone N,N-dimethylhydrazone 6 and the chiral iodides (R)-3 or (S)-3, derived from the enantiomers of ethyl β-hydroxybutyrate, controlling the estereocenter at C-2 of the molecules. The alkylated products 7 and 7a were easily transformed into the 1,8-O-TBS-1,8-dihydroxy-5-nonanones 9 and 9a in four steps, and a subsequent stereoselective spiroketalization, in acidic media, afforded a Z:E mixture (1:2) of compounds 1 and 1a.
Efficient synthesis of the ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer
Budin, Noah,Higgins, Erin,DiBernardo, Anthony,Raab, Cassidy,Li, Chun,Ulrich, Scott
, p. 560 - 564 (2018)
The ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer were prepared in a short, operationally simple synthetic sequence from racemic β-butyrolactone. Enantioselective hydrolysis of β-butyrolactone with immobilized Candida antarctica lipase-B (CAL-B) results in (R)-β-butyrolactone and (S)-β-hydroxybutyric acid, which are easily converted to (R) or (S)-ethyl-3-hydroxybutyrate and reduced to (R) or (S)-1,3 butanediol. Either enantiomer of ethyl-3-hydroxybutyrate and 1,3 butanediol are then coupled, again using CAL-B, to produce the ketone body ester product. This is an efficient, scalable, atom-economic, chromatography-free, and low cost synthetic method to produce the ketone body esters.
Enantioselective Production of (S)-3-Hydroxybutyric Acid, (S)-1,3-Butanediol and (R)-1,3-Butanediol Using Methanol Yeast
Matsumura, Shuichi,Imafuku, Hiroshi,Takahashi, Yoshinori,Toshima, Kazunobu
, p. 251 - 254 (1993)
(S)-3-Hydroxybutyric acid and (S)-1,3-butanediol were obtained by the treatment of 1,3-butanediol with the resting cells of methanol yeast, Candida boidinii (IFO 10574). (R)-1,3-Butanediol was also obtained in high optical purity by the enantioselective reduction of 4-hydroxy-2-butanone in the presence of methanol using the same methanol yeast.
SYNTHESIS OF 3-HYDROXYBUTYRYL 3-HYDROXYBUTYRATE AND RELATED COMPOUNDS
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Paragraph 0308; 0317, (2021/04/02)
In various embodiments methods of preparing hydroxybutyryl 3-hydroxybutyrate and related compounds are provided along with methods of use thereof.
Enantioselective hydrogenation of ketones over a tartaric acid-modified raney nickel catalyst: Substrate-modifier interaction strength and enantioselectivity
Choliq, Azka Azkiya,Murakami, Eitaro,Yamamoto, Shota,Misaki, Tomonori,Fujita, Morifumi,Okamoto, Yasuaki,Sugimura, Takashi
, p. 1325 - 1332 (2018/09/21)
Chiral (R,R)-tartaric acid and NaBr-doubly modified Raney nickel (TA-MRNi) is a promising heterogeneous catalyst for enantioselective hydrogenation of prochiral β-keto esters. To obtain deeper insights into the factors ruling the enantioselectivity, enantiodifferentiating hydrogenation of substituted ketones was studied over TA-MRNi and NaBr-modified RNi by use of combined individual-competitive hydrogenation techniques. Relative equilibrium adsorption constants of the substrates were estimated to evaluate their relative interaction strength with adsorbed tartaric acid moiety. DFT calculations were also performed to estimate the interaction energy through hydrogen bonding, providing clear support to the kinetic analysis and surface model. It is concluded with the enantioselective hydrogenation of ketones over TA-MRNi that the enantioselectivity increases as the substrate-modifier interaction strength increases: Methyl acetoacetate (MAA) > acetylacetone (AA) ～ 4-hydroxy-2-butanone (HB) > 2-octanone (2O).
