121404-60-2Relevant academic research and scientific papers
Efficient large scale stereoinversion of (R)-ethyl 3-hydroxybutyrate
Carnell, Andrew J.,Head, Robert,Bassett, Derek,Schneider, Michael
, p. 821 - 825 (2007/10/03)
A three step method for the large scale preparation of enantiomerically pure ethyl (S)-3-hydroxybutyrate is reported starting from the commercial biopolymer poly[(R)-hydroxybutyrate]. The key step depends on the ability to cleanly invert the stereochemistry of (R)-ethyl 3-hydroxybutyrate via its mesylate ester under neutral conditions, avoiding the competing elimination process. This has been achieved in good (75%) yield on >100g scale by controlled addition of the mesylate to a stirred slurry of calcium carbonate in water at 80°C.
Preparation of optically active β-amino acids from microbial polyester polyhydroxyalkanoates
Park, Sang Hyun,Lee, Seung Hwan,Lee, Sang Yup
, p. 498 - 499 (2007/10/03)
An efficient method for the preparation of optically active ethyl β-aminobutyrate from the biopolymer, poly-(R)-(-)-3-hydroxybutyrate (PHB) obtained from bacterial cells has been established using chemical transforamtions: simple recovery of PHB from bacterial cells followed by acidic alcoholysis, tosylation, nucleophilic substitution by azide, and an indium mediated reduction.
Synthesis of (+)-Turmeronol A, an Inhibitor of Soybean Lipoxygenase, and (+)-ar-Turmerone
Kitahara, Takeshi,Furusho, Yoshio,Mori, Kenji
, p. 1137 - 1140 (2007/10/02)
Syntheses of optically pure turmeronol A and turmerone were achieved in a simple manner starting from ethyl (R)-3-hydroxybutanoate (4) of 100percent e.e.The key step was the displacement of the chiral tosylate (6) with an organocopper reagent.
THE USE OF METHYL SUBSTITUTED CHIRAL SYNTHONS IN THE SYNTHESIS OF PINE SAWFLIES PHEROMONES
Larcheveque, Marc,Sanner, Caroline,Azerad, Robert,Buisson, Didier
, p. 6407 - 6418 (2007/10/02)
The preparation of methyl-substituted synthons of high enantiomerical purities by Claisen transposition, cuprate substitution of secondary optically active alcohols and microbial reduction of β-ketoesters was investigated and applied to the synthesis of (2S,3S,7S) and (2S,3R,7R)-3,7-dimethylpentadecan-2-ol, the pheromones of diprionid species of pine sawflies.
