37505-07-0

Usage

Uses

(2S)-2-Hydroxy-2-methylbutanoic Acid is a useful building block for organic synthesis.

Upstream product

• 3739-30-8 2-hydroxy-2-methylbutyric acid 
• 130478-73-8 (S)-5-Ethyl-5-methyl-3-((S)-1-phenyl-ethyl)-oxazolidin-4-one 
• 107365-50-4 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-N-((S)-1-methoxymethyl-2-methyl-propyl)-2-methyl-butyramide 
• 74-90-8 hydrogen cyanide 
• 78-93-3 butanone 
• 508-67-8 germerine 
• 691359-47-4 (S)-2-hydroxy-2-methyl-4-(phenylthio)butanoic acid 
• 552888-23-0 (S)-3-hydroxytetrahydrothiophene-3-carboxylic acid 
• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 
• 130478-69-2 (E)-2-Methyl-but-2-enoic acid hydroxymethyl-((S)-1-phenyl-ethyl)-amide 
• 130478-67-0 (E)-2-Methyl-but-2-enoic acid ((S)-1-phenyl-ethyl)-amide 
• 128549-11-1 2-Benzyloxy-2-methyl-butyric acid methyl ester 
• 691890-02-5 (S)-2-hydroxy-2-methyl-4-phenylthiobutyronitrile 
• 107365-39-9 (S)-2-tert-Butoxy-N-((S)-1-methoxymethyl-2,2-dimethyl-propyl)-2,N-dimethyl-butyramide 

Downstream Products

• 455878-44-1 (S)-1-ethyl-1-methyl-2-[(4-methylsulfonyl)phenyl]-2-oxoethyl 2-(1-methylethoxy)acetate 
• 189954-93-6 (S)-5-ethyl-5-methyl-3-(1-methylethoxy)-4-[(4-methylsulfonyl)phenyl]-3-oxolen-2-one 
• 455878-43-0 (S)-1-ethyl-1-methyl-2-[(4-methylthio)phenyl]-2-oxoethyl 2-(1-methylethoxy)acetate 
• 499140-48-6 (S)-5-ethyl-5-methyl-3-(1-methylethoxy)-4-(4-(methylthio)phenyl)-3-oxolen-2-one 
• 455878-42-9 (S)-2-hydroxy-2-methyl-1-[4-(methylthio)phenyl]butan-1-one 
• 499140-47-5 (S)-5-ethyl-4-hydroxy-5-methyl-3-(1-methylethoxy)-3-oxolen-2-one 
• 857665-62-4 (S)-benzyl 2-[(diphenylphosphino)oxy]-2-methylbutyrate 
• 587832-08-4 benzyl (S)-(+)-2-hydroxy-2-methylbutanoate 

Relevant academic research and scientific papers

UTILISATION DES ALCOXYTRIALKYLALUMINATES EN SYNTHESE ASYMETRIQUE: SYNTHESE DE L'ACIDE HYDROXY-2, METHYL-2 BUTANOIQUE ENANTIOMERIQUEMENT ENRICHI EN R OU S

The reaction of LiAlEt3OR* with (-)-menthyl pyruvate (R*OH = (-)-N-methylephedrine) and with (+)-menthyl pyruvate (R*OH = (+)-N-methylephedrine) in hexane/ether as solvent produces the corresponding 2-hydroxy-2-methylbutan

Linum usitatissimum hydroxynitrile lyase cross-linked enzyme aggregates: A recyclable enantioselective catalyst

An immobilized form of the hydroxynitrile lyase from Linum usitatissimum (LuHNL) as cross-linked enzyme aggregate (CLEA) with high specific activity (303.5 U/g) and recovery (33%) was developed. Molecular imprinting using 2-butanone as additive in the immobilization process improved the synthetic activity of the biocatalyst. LuCLEA could be partially recycled for the synthesis of (R)-2-butanone cyanohydrin on a preparative scale over two batches. The enantioenriched cyanohydrin obtained was further hydrolyzed to give (R)-2-hydroxy-2-methylbutyric acid in 85% yield (from 2-butanone) and 87% ee.

Stereoselective biocatalytic synthesis of (S)-2-hydroxy-2-methylbutyric acid via substrate engineering by using "thio-disguised" precursors and oxynitrilase catalysis

3-Tetrahydrothiophenone (4) and 4-phenylthiobutan-2-one (7) were used as masked 2-butanone equivalents to give the corresponding cyanohydrins 5 (79% yield, 91% ee) and 8 (95% yield, 96% ee) in an enzymatic cyanohydrin reaction applying the hydroxynitrile

Process for the preparation of chiral α-hydroxycarboxylic acids

A process for the preparation of chiral α-hydroxycarboxylic acids: in which R1 is optionally halogen substituted C1-C2-alkyl and R2 is optionally halogen substituted C2-C3-alkyl from a compound: in which R′

Practical enantioselective synthesis of a COX-2 specific inhibitor

Two synthetic strategies to the COX-2 specific inhibitor 1 have been described that allowed its preparation in large quantities in 79% overall yield from (S)-2-hydroxy-2-methylbutyric acid. These studies have led to the identification of an efficient resolution of (±)-2-hydroxy-2-methylbutyric acid and a novel thionyl chloride aided formation of amide 11 from acid 6.

Enzyme-catalyzed synthesis of (R)-ketone-cyanohydrins and their hydrolysis to (R)-α-hydroxy-α-methyl-carboxylic acids

(R)-Ketone-cyanohydrins (R)-2 are obtained with high enantioselectivity from aliphatic ketones 1 and HCN in organic solvents using (R)-oxynitrilase ( EC 4.1.2.10) as catalyst. Acid catalyzed hydrolysis of the cyanohydrins (R)-2 affords the corresponding (R)-α-hydroxy-α-methyl-carboxylic acids (R)-3 without measurable racemization.

Functionalisation of Unsaturated Amides: Synthesis of Chiral α- or β-Hydroxy Acids

Mercury cyclisation of hemiamidals containing a stereogenic centre affords diastereoisomeric mixtures of tetrahydro-1,3-oxazin-4-ones or oxazolidin-4-ones, which are easily separated by silica gel chromatography and hydrolysed to give chiral α- and β-hydroxy acids.

Enzymatic Preparation of Enantiomerically Enriched Tertiary α-Benzyloxy Acid Esters. Application to the Synthesis of (S)-(-)-Frontalin

Enzymatic preparation of enantiomerically enriched tertiary α-benzyloxy acid esters is described.Enantioselective hydrolysis of the racemic esters of the formula by lipase OF (from Candida cylindracea, Meito Sangyo Co.) was succes

ELECTROPHILIC ASYMMETRIC SYNTHESES OF α-HYDROXY CARBOXYLIC ACIDS

Asymmetric electrophilic syntheses of α-hydroxy carboxylic acids from chiral amide derivatives of tert-butyl- and trialkylsilyl- protected glycolic and lactic acids are described which lead to chiral α-hydroxy carboxylic acids in 60-95percent diastereomeric excess.