121404-60-2Relevant articles and documents
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.
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.