72450-34-1

Usage

Uses

Methyl 2-hydroxy-2-methyl-3-oxobutyrate may be used in chemical synthesis.

InChI:InChI=1/C6H10O4/c1-4(7)6(2,9)5(8)10-3/h9H,1-3H3

Upstream product

• 37037-89-1 Methyl-3-hydroxy-3-methyl-2-oxobutyrat 
• 600-22-6 pyruvic acid methyl ester 
• 113-24-6 sodium pyruvate 
• 105-45-3 acetoacetic acid methyl ester 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 6622-76-0 methyl (E)-2-methyl-2-butenoate 

Relevant academic research and scientific papers

Aerobic α-hydroxylation of β-keto esters and amides by co-catalysis of SmI3 and I2 under mild base-free conditions

A clean base-free α-hydroxylation of β-keto esters and amides has been developed, in which air was used as the oxygen source and SmI3 and I2 were applied as the catalysts, affording the corresponding α-hydroxylated 1,3-dicarbonyl pro

Extended reaction scope of thiamine diphosphate dependent cyclohexane-1,2-dione hydrolase: From C-C bond cleavage to C-C bond ligation

ThDP-dependent cyclohexane-1,2-dione hydrolase (CDH) catalyzes the CC bond cleavage of cyclohexane-1,2-dione to 6-oxohexanoate, and the asymmetric benzoin condensation between benzaldehyde and pyruvate. One of the two reactivities of CDH was selectively knocked down by mutation experiments. CDH-H28A is much less able to catalyze the CC bond formation, while the ability for CC bond cleavage is still intact. The double variant CDH-H28A/N484A shows the opposite behavior and catalyzes the addition of pyruvate to cyclohexane-1,2-dione, resulting in the formation of a tertiary alcohol. Several acyloins of tertiary alcohols are formed with 54-94% enantiomeric excess. In addition to pyruvate, methyl pyruvate and butane-2,3-dione are alternative donor substrates for CC bond formation. Thus, the very rare aldehyde-ketone cross-benzoin reaction has been solved by design of an enzyme variant.

Cerium-catalyzed α-hydroxylation reactions of α-cyclopropyl β-dicarbonyl compounds with molecular oxygen

Three α-cyclopropyl β-dicarbonyl compounds have been used as probes for α-radicals as electrophilic reaction intermediates in a cerium-catalyzed α-hydroxylation reaction with molecular oxygen. Since the cyclopropyl group did not ring-open to products with a butenyl moiety, but was retained in the products, a localized unpaired electron at the α position can be excluded during the course of the reaction. The α-cyclopropyl- substituted substrates were prepared by aldol or Claisen reactions. Other substrates with α-methyl, α-isopropyl, and α-tert-butyl substituents were prepared and converted under the α-hydroxylation conditions in order to estimate steric influences on the yield of the reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

A New Synthesis of Methyl α-Acetolactate based on Thiazolium Chemistry and modelled on the Enzymatic Synthesis of α-Acetolactate catalysed by Acetolactate Synthase

Methyl α-acetolactate has been synthesised via a series of adducts with benzothiazole in a manner analogous to the enzymatic reaction catalysed by acetolactate synthase.

Synthesis of 2-Hydroxy-3-oxocarboxylic Esters From the Corresponding α,β-Unsaturated Esters by a Simple One-Step Procedure

A convenient one-step synthesis of 2-alkyl-2-hydroxy-3-oxocarboxylic esters by potassium permanganate oxidation of the corresponding readily available α,β-unsaturated esters is described.Preparation of the latter by the phosphonate modification of the Wit

Catalysis by Di-n-butyltin Oxide of a Tertiary Ketol Rearrangement: Synthesis of Intermediates and Analogues of Valine and Isoleucine Biosynthesis

Di-n-butyltin oxide efficiently catalyses the rearrangement of 3-hydroxy-2-oxocarboxylic acid ester into the corresponding 2-hydroxy-3-oxo-esters, in a reaction that simulates the reversible rearrangement catalysed by the enzyme reductoisomerase.