CAS 72657-23-9: (R)-(-)-methyl B-hydroxyisobutyrate

Applications Chiral derivative of 3-Hydroxyisobutyrate. References Waldmann, H., et al.: Bioorg. Med. Chem., 2, 477 (1994), Vonstein, V., et al.: J. Bacteriol., 177, 4540 (1995),

(R)-3-Hydroxyisobutyric acid methyl ester is a retronecine analogue that can be synthesized by hydrozirconation of an (R)-3-hydroxyisobutyryl chloride. The synthesis starts with the stereoselective formation of an acid lactone from a chiral intramolecular Diels-Alder reaction between a cyclic enol ether and a butenolide. This lactone is then converted to the desired product by lactonization followed by anion formation and mismatch elimination. The final step involves alkylation of the olefin with methyllithium, followed by acid hydrolysis to give the desired product.

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(R)-(-)-3-Hydroxy-2-methylpropionic acid methyl ester