22146-57-2

Basic information

• Product Name: (R)-Trimethyllactic acid
• Synonyms: (R)-(-)-3,3-Dimethyl-2-hydroxybutyric acid;(R)-2-Hydroxy-3,3-dimethylbutanoic acid;(R)-Trimethyllactic acid;(2R)-2-Hydroxy-3,3-dimethylbutanoic acid;[R,(-)]-2-Hydroxy-3,3-dimethylbutyric acid
• CAS NO: 22146-57-2
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• Mol File: 22146-57-2.mol

Chemical Properties

• Boiling Point: 242 ºC
• Flash Point: 115 ºC
• Appearance: /
• Density: 1.100
• Vapor Pressure: 0.00583mmHg at 25°C
• Refractive Index: 1.459
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-Trimethyllactic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Trimethyllactic acid(22146-57-2)
• EPA Substance Registry System: (R)-Trimethyllactic acid(22146-57-2)

Safety Data

• Hazardous Substances Data: 22146-57-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
(R)-Trimethyllactic acid is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block in the production of specialty chemicals.
Used in Pharmaceutical Industry:
(R)-Trimethyllactic acid is used as a pharmaceutical intermediate for the development of drugs. Its properties make it a valuable component in the synthesis of new therapeutic agents, potentially contributing to the treatment of various medical conditions.

InChI:InChI=1/C6H12O3/c1-6(2,3)4(7)5(8)9/h4,7H,1-3H3,(H,8,9)/t4-/m0/s1

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 20859-02-3 L-tert-Leucine 
• 815-17-8 trimethylpyruvic acid 
• 30263-65-1 1,1-dibromo-3,3-dimethylbutan-2-one 
• 346424-16-6 (2R)-ethyl 2-hydroxy-3,3-dimethylbutanoate 
• 26782-71-8 D-tert-leucine 
• 5333-74-4 ethyl 3,3-dimethyl-2-oxobutanoate 

Downstream Products

• 486394-64-3 [4-Chloro-2-({[(S)-1-((R)-2-hydroxy-3,3-dimethyl-butyryl)-azetidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid tert-butyl ester 
• 439117-45-0 [4-Chloro-2-({[(S)-1-((R)-2-hydroxy-3,3-dimethyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid tert-butyl ester 
• 885722-42-9 (R)-benzyl (3,3-dimethyl-2-hydroxybutanoate) 
• 885722-44-1 (R,R)-phthalic acid bis(1-vhlorocarbonyl-2,2-dimethyl-propyl) ester 
• 885722-58-7 (R,R)-phthalic acid bis(1-carboxy-2,2-dimethyl-propyl) ester 
• 885722-43-0 (R,R)-phthalic acid bis(1-benzyloxycarbonyl-2,2-dimethyl-propyl) ester 
• 885722-52-1 (R,R)-phthalic acid bis{1-[3-(diphenyl-phosphinoyl)-2-iodo-phenoxycarbonyl]-2,2-dimethylpropyl} ester 
• 885722-53-2 (R,R)-phthalic acid bis{1-[3-(diphenyl-phosphinoyl)-2-iodo-4-methoxy-phenoxycarbonyl]-2,2-dimethylpropyl} ester 
• 885722-55-4 (R,R)-phthalic acid bis{1-[3-(diphenyl-phosphinoyl)-2-iodo-4-phenyl-phenoxycarbonyl]-2,2-dimethylpropyl} ester 
• 885722-54-3 (R,R)-phthalic acid bis{1-[3-(diphenyl-phosphinoyl)-2-iodo-4-p-tolyloxy-phenoxycarbonyl]-2,2-dimethylpropyl} ester 
• 885722-56-5 (R,R)-phthalic acid bis{1-[3-(diphenyl-phosphinoyl)-2-iodo-4-mesityl-phenoxycarbonyl]-2,2-dimethylpropyl} ester 
• 1201686-64-7 (5S)-N-[5-chloro-2-(1H-tetrazol-1-yl)benzyl]-1-[(2R)-2-hydroxy-3,3-dimethylbutanoyl]-4,5-dihydro-1H-pyrazole-5-carboxamide 
• 1097133-05-5 (1R,3S,5R)-2-((R)-2-hydroxy-3,3-dimethylbutyryl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 
• 1097133-07-7 (1S,3S,5S)-2-((R)-2-hydroxy-3,3-dimethylbutyryl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide 

Relevant articles and documents

Asymmetric hydrogenation reaction of alpha-ketoacids compound

The invention relates to the technical field of organic chemistry, especially to an asymmetric hydrogenation reaction of an alpha-ketoacids compound. The asymmetric hydrogenation reaction comprises a scheme shown in the description. In the scheme, R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, C1-C6 alkyl, or aralkyl; a substituent group is C1-C6 alkyl, C1-C6 alkoxy, or halogen; and the number of the substituent group is 1-3. In the scheme, M is a chiral spiro-pyridylamino phosphine ligand iridium complex having a structure shown in the description. In the structure, R is hydrogen, 3-methyl, 4-tBu, or 6-methyl.

Reaction intermediate analogues as bisubstrate inhibitors of pantothenate synthetase

The biosynthesis of pantothenate, the core of coenzyme A (CoA), has been considered an attractive target for the development of antimicrobial agents since this pathway is essential in prokaryotes, but absent in mammals. Pantothenate synthetase, encoded by the gene panC, catalyzes the final condensation of pantoic acid with β-alanine to afford pantothenate via an intermediate pantoyl adenylate. We describe the synthesis and biochemical characterization of five PanC inhibitors that mimic the intermediate pantoyl adenylate. These inhibitors are competitive inhibitors with respect to pantoic acid and possess submicromolar to micromolar inhibition constants. The observed SAR is rationalized through molecular docking studies based on the reported co-crystal structure of 1a with PanC. Finally, whole cell activity is assessed against wild-type Mtb as well as a PanC knockdown strain where PanC is depleted to less than 5% of wild-type levels.

Direct asymmetric hydrogenation of α-keto acids by using the highly efficient chiral spiro iridium catalysts

A new efficient and highly enantioselective direct asymmetric hydrogenation of α-keto acids employing the Ir/SpiroPAP catalyst under mild reaction conditions has been developed. This method might be feasible for the preparation of a series of chiral α-hydroxy acids on a large scale.

N-heterocyclic bicyclic lactone compounds

Novel N-heterocyclic bicyclic lactone compounds of formula I and its novel hydroxyamide precursors of formula IV, are synthesized by coupling a hydroxy acid of formula II with an ester of formula III or a pharmaceutically acceptable salt thereof, in the presence of a peptide coupling reagent to produce a hydroxyamide of formula IV, and cyclizing the hydroxyamide of formula IV to produce compounds of formula 1.

Stereoselective synthesis of a potent thrombin inhibitor by a novel P2-P3 lactone ring opening

The concise synthesis of a potent thrombin inhibitor was accomplished by a mild lactone aminolysis between an orthogonally protected bis-benzylic amine and a diastereomerically pure lactone. The lactone was synthesized by the condensation of L-proline met

Thrombin inhibitors

Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: or a pharmaceutically acceptable salt thereof, e.g. 1-(3(S)-Cyclopropyl-2(R)-hydroxybutanoyl)azetidine-2(S)-N-(2-aminomethyl-5-chlorobenzyl)carboxamide, and 1-(3-Cyclopropyl-3-methyl-2(R)-hydroxybutanoyl)azetidine-2(S)-N-(2-aminomethyl-5-chlorobenzyl)carboxamide.

Thrombin inhibitors

Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: or a pharmaceutically acceptable salt thereof, e.g. 1-(3(S)-Cyclopropyl-2(R)-hydroxybutanoyl)azetidine-2(S)-N-(2-aminomethyl-5-chlorobenzyl)carboxamide, and 1-(3-Cyclopropyl-3-methyl-2(R)-hydroxybutanoyl)azetidine-2(S)-N-(2-aminomethyl-5-chlorobenzyl)carboxamide.

Thrombin inhibitors

Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: or a pharmaceutically acceptable salt thereof, e.g. where R3 is —CH2NH2, —CH2CH2NH2, or —CH2NHC(O)OC(CH3)3.

Enantioseparation of racemic organic ammonium perchlorates by a silica gel bound optically active di-tert-butylpyridino-18-crown-6 ligand

Both enantiomers of the novel chiral di-tert-butylpyridino-18-crown-6 ligand (R,R)-7 and (S,S)-7 containing an allyloxy group on the pyridine subcyclic unit were prepared by the reaction of 4-allyloxy-2,6-pyridinedimethyl ditosylate 9 and the enantiomers of di-tert-butyl-substituted tetraethylene glycol (R,R)-8 and (S,S)-8 in the presence of a strong base. One of them, (R,R)-7, was covalently attached to silica gel, and this chiral stationary phase (CSP) separated four selected racemic organic ammonium perchlorates into their enantiomers by column chromatography.

Polyfunctional (R)-2-Hydroxycarboxylic Acids by Reduction of 2-Oxo Acids with Hydrogen Gas or Formate and Resting Cells of Proteus vulgaris

Various (R)-2-hydroxy acids such as (R)-2-hydroxy-3-enoic-, 3,5-dienoic-, 4-oxo-, (R,S)-3-hydroxy and some others were prepared on a scale up to 0.12 mol by biocatalytic reduction of the corresponding 2-oxo acids with P. vulgaris and hydrogen gas and/or formate as electron donors.With the exception of the 2-hydroxy-4-oxo acids it could be proved that the enantiomeric excess is >97 percent.For the 4-oxo derivatives this enantiomeric excess can be assumed.The yields of isolated products are high because they were isolated from rather small amounts of biocatalyst and low buffer concentrations.Product concentrations in the range of 0.1- 0.24 M were obtained.For 1 mmol of product formation in 15-20 h about 20-40 mg (dry weight) of P. vulgaris cells are necessary.