119596-06-4

Usage

Classification

Heterocyclic compound

Isomer

Isomer of 3-Isoxazolemethanol, alpha,5-dimethyl-, (R)(9CI)

Structure

Derivative of isoxazole, a five-membered ring with three carbon atoms, one oxygen atom, and one nitrogen atom

Enantiomer

Designated as "S," indicating the S enantiomer, making it chiral and capable of existing in two mirror-image forms

Potential Applications

Pharmaceutical and chemical industries for its unique structure and properties

Upstream product

• 24068-54-0 3-acetyl-5-methylisoxazole 

Relevant academic research and scientific papers

Chemoenzymatic Synthesis of Chiral Isoxazole Derivatives

The synthesis of the two enantiomers of 1-(3-bromo-5-isoxazolyl)-2-(tert-butylamino)ethanol (1), a potent and selective β2-adrenergic stimulant, has been efficiently accomplished by enzyme-catalyzed transformations.The absolute configurations are attributed to (+)- and (-)-1 by correlation with (S)-3-butyn-2-ol.The S enantiomer was prepared in >98percent enantiomeric excess by reducing α-bromo ketone 4 in the presence of alcohol dehydrogenase from Thermoanaerobium brockii and the R enantiomer was obtained in 97percent ee through a kinetic resolution of the racemic bromohydrin(+/-)-5, in organic solvents, catalyzed by lipase P from Pseudomonas fluorescens.The experimental conditions for the lipase-catalyzed asymmetric transesterifications were optimized in order to improve reaction rates and the enantiomeric excess of the products.