4026-20-4

Usage

Uses

Used in Medical Research:
2-Hydroxy-3,3-dimethylbutyric acid is utilized as a potential biomarker for liver fibrosis, aiding in the identification and monitoring of this condition.
Used in Pharmaceutical Development:
As a building block in the synthesis of various pharmaceuticals, 2-hydroxy-3,3-dimethylbutyric acid contributes to the creation of new medications and therapeutic agents.
Used in Metabolic and Inflammatory Disorder Management:
2-Hydroxy-3,3-dimethylbutyric acid is studied for its potential role in managing inflammatory and metabolic disorders, suggesting its use as a therapeutic agent in these areas.
Used in Organic Compound Synthesis:
In the chemical industry, 2-hydroxy-3,3-dimethylbutyric acid is used as a building block for synthesizing a range of organic compounds, highlighting its versatility in compound development.

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

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 38895-88-4 1-hydroxy-3,3-dimethylbutan-2-one 
• 50364-40-4 2-bromo-2-tert-butyl acetic acid 
• 30263-65-1 1,1-dibromo-3,3-dimethylbutan-2-one 
• 815-17-8 trimethylpyruvic acid 
• 36156-92-0 2-t-butyl-2-hydroperoxyacetic acid 
• 31469-23-5 2-(tert-butyl)-1,1-bis(trimethylsilyloxy)ethene 
• 507-20-0 tertiary butyl chloride 
• 69097-20-7 tris(trimethylsilyloxy)ethylene 
• 33350-17-3 2-hydroxy-3,3-dimethylbutyronitrile 
• 41262-30-0 1,1,1-trichloro-3,3-dimethyl-2-butanol 
• 74-89-5 methylamine 
• 74-90-8 hydrogen cyanide 
• 64-17-5 ethanol 

Downstream Products

• 563-80-4 3-methyl-butan-2-one 
• 53607-03-7 2,4,6-tris(tert-butyl)-1,3,5-trioxane 
• 114738-52-2 5,5-dimethyl-4-hydroxy-1-phenyl-1-hexen-3-one 
• 75-98-9 Trimethylacetic acid 
• 630-19-3 pivalaldehyde 
• 121129-31-5 (+/-)-methyl (2-hydroxy-3,3-dimethyl)butyrate 
• 815-17-8 trimethylpyruvic acid 
• 1558755-42-2 9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one 

Relevant academic research and scientific papers

1,3-Diastereocontrol in acyclic radical allylations

The radical allylation of an acyclic α-hydroxyketone with allyltributyltin under chelation-controlled conditions is reported. Several reaction conditions were explored, including radical initiators, solvents, and temperatures to improve the yield and the diastereomeric ratio. Some Lewis acids, like magnesium bromide etherate and zinc chloride, gave superior diastereomeric ratios (up to 100:1) and good yields.

Preparation method of 3, 3-dimethyl-2-oxobutyric acid and triazinone

The invention relates to the field of pesticides, and discloses a preparation method of 3, 3-dimethyl-2-oxobutyric acid and triazinone. The preparation method of the 3, 3-dimethyl-2-oxobutyric acid provided by the invention comprises the step of oxidizing the 3, 3-dimethyl-2-oxobutyric acid and/or a salt thereof by taking oxygen-containing gas as an oxidizing agent in the presence of a catalyst under the condition that the pH value is 7-13. According to the method disclosed by the invention, the 3, 3-dimethyl-2-hydroxybutyric acid and/or the salt thereof is taken as the raw material, and oxygen or air is used for replacing other oxidants, so that high-salinity wastewater and solid waste are avoided, the cost of the raw material is reduced, and the method is simple to operate and suitable for industrial production.

Preparation method of 3,3-dimethyl-2-oxobutyric acid

The invention relates to a preparation method of 3,3-dimethyl-2-oxobutyric acid, and belongs to the technical field of pharmaceutical intermediate synthesis. In order to solve the problems of seriouspollution and low yield of the existing synthetic route, the invention provides a preparation method of 3,3-dimethyl-2-oxobutyric acid, and the method comprises: halogenating 3,3-dimethyl butyric acidwith a halogenating agent in an organic solvent to obtain an intermediate product; then carrying out a hydrolysis reaction to obtain a corresponding hydrolyzed product; and in the presence of TEMPO catalyst, oxidizing the hydrolyzed product under the action of an oxidant, and then carrying out acidification to obtain a product 3,3-dimethyl-2-oxobutyric acid. According to the preparation method provided by the invention, a mixed catalyst of a noble metal catalyst and a transition metal catalyst is avoided, the environmental pollution and the cost are reduced, and the effects of high yield andhigh purity can still be ensured.

Metal-free one-pot α-carboxylation of primary alcohols

An efficient metal-free procedure for the formal α-carboxylation of primary alcohols has been developed. The method involves a one-pot oxidation/Passerini/hydrolysis sequence and provides access to α-hydroxy acids bearing a broad range of functional groups. A minor modification to the reaction conditions extends the range of accessible products to α-hydroxy esters.

Chiral propargylic cations as intermediates in SN1-type reactions: Substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity

Nine propargylic acetates, bearing a stereogenic center (-C*HXR 2) adjacent to the electrophilic carbon atom, were prepared and subjected to SN1-type substitution reactions with various silyl nucleophiles employing bismuth trifluoromethanesulfonate [Bi(OTf)3] as the Lewis acid. The diastereoselectivity of the reactions was high when the alkyl group R2 was tertiary (tert-butyl), irrespective of the substituent X. Products were formed consistently with a diastereomeric ratio larger than 95:5 in favor of the anti-diastereoisomer. If the alkyl substitutent R2 was secondary, the diastereoselectivity decreased to 80:20. The reaction was shown to proceed stereoconvergently, and the relative product configuration was elucidated. The reaction outcome is explained by invoking a chiral propargylic cation as an intermediate, which is preferentially attacked by the nucleophile from one of its two diastereotopic faces. Density functional theory (DFT) calculations suggest a preferred conformation in which the group R2 is almost perpendicular to the plane defined by the three substituents at the cationic center, with the nucleophile approaching the electrophilic center opposite to R2. Transition states calculated for the reaction of allyltrimethylsilane with two representative cations support this hypothesis. Tertiary propargylic cations with a stereogenic center (-C* HXR2) in the α position were generated by ionization of the respective alcohol precursors with FSO3H in SO2ClF at -80 C. Nuclear magnetic resonance (NMR) spectra were obtained for five cations, and the chemical shifts could be unambiguously assigned. The preferred conformation of the cations as extracted from nuclear Overhauser experiments is in line with the preferred conformation responsible for the reaction of the secondary propargylic cations.

Stereospecific α-methallylation of hydroxyaldehydes by silatropic ene cyclisation

We describe the thermal rearrangement of aldehydes bearing an α-(allyl- or crotylsilyl)oxy substituent. The transformations are best described mechanistically as intramolecular silatropic ene reactions based on stereoselectivity, kinetic and computed transition state data. The overall process constitutes a stereospecific (meth)allylation of α-hydroxyaldehydes, under neutral conditions, in which the hydroxyl protecting group is also the (meth)allylating agent.

The design and synthesis of inhibitors of pantothenate synthetase

Pantothenate synthetase catalyses the ATP-dependent condensation of d-pantoate and β-alanine to form pantothenate. Ten analogues of the reaction intermediate pantoyl adenylate, in which the phosphodiester is replaced by either an ester or sulfamoyl group, were designed as potential inhibitors of the enzyme. The esters were all modest competitive inhibitors, the sulfamoyls were more potent, consistent with their closer structural similarity to the pantoyl adenylate intermediate. The Royal Society of Chemistry 2006.

Reaction of carboxylic acids with diethyl phosphorocyanidate; a novel synthesis of homologated α-hydroxycarboxylic acids from carboxylic acids

Carboxylic acids react with 2 equivalents of diethyl phosphorocyanidate in the presence of triethylamine to give dicyanophosphates in good yields; these dicyanophosphates can be hydrolyzed easily to give homologated α- hydroxycarboxylic acids.

Protocols for the Preparation of Each of the Four Possible Stereoisomeric α-Alkyl-β-hydroxy Carboxylic Acids from a Single Chiral Aldol Reagent

Protocols have been devised whereby all four possible stereoisomeric α-alkyl-β-hydroxy carboxylic acids can be derived from a single aldol reagent, hydroxy ketone 3.Compound 3, obtained in enantiomerically homogeneous form in 50percent overall yield from tert-butylglycine (1), is used for aldol reactions in the form of its trimethylsilyl and tert-butyldimethylsilyl derivatives, 4 and 5.The Z lithium and Z boron enolates of 4 react with various aldehydes to give aldols 8 and 9, respectively.Deprotonation of 4 by bromomagnesium 2,2,6,6-tetramethylpiperidide (MTMP) gives the E enolate, which may be trapped by trimethylsilyl chloride to obtain the E silyl enol ether 11.The E bromomagnesium enolate of 4 reacts with aldehydes to give aldols of structure 15.Transmetalation of the bromomagnesium enolate of keto ether 5 is accomplished by reaction with (triisopropoxy)titanium chloride.The resulting E (triisopropoxy)titanium enolate reacts with aldehydes to provide aldols of structure 17.The aldols resulting from the foregoing reactions are hydrolyzed to keto diols 19-22, which are oxidized to the stereoisomeric α-methyl-β-hydroxy carboxylic acids 23-26.

Synthesis of a Chiral, Nonracemic Aziridinone (α-Lactam)

(S)-tert-Leucine is diazotized affording a mixture of the expected α-chloro and α-hydroxy acids (S)-15 and (S)-16 and the rearranged β-chloro and β-hydroxy acids (R)-12 and (S)-11.Separation produces a 51percent yield of pure (S)-15 (e.e. >= 97.4percent) which is converted via the acid chloride (S)-17 into the α-chloro amides (S)-18a and b (e.e. = 99.0 and 95.2percent, respectively).On treatment with tBuOK, the latter is converted into the α-lactam (R)-22b (59percent, e.e. >= 91.0percent, D20 = -293.7), which is accompanied by small amounts of its ring opening product (R)-23b.Only the α-amino ester (R)-23a is formed from the α-chloro amide (S)-18a and tBuOK.While the enantiomers of the halo amides 13, 18a, b, 24a, b and of the 3-pentyl esters of the hydroxy acid 16 are separated by GC on chiral columns, the α-lactam 22b and the α-amino esters 23a, b require conversion into separable derivatives without involving the stereogenic center.Thus, alkaline hydrolysis of 22b as well as acidic cleavage of 23 yield the α-amino acids 25 which are cyclized to the oxazolidine-2,5-diones 26 by means of bis(trichloromethyl)carbonate ("triphosgene").As shown by the high enantiomeric excess of the products derived from (S)-tert-leucine none of the reactions described results in a considerable degree of racemization.Authentic samples of 11 and 12 are synthesized from the Reformatzky product 21.The absolute configurations of the major enantiomers derived from (S)-14 are based on the retention on chiral GC columns, the signs of optical rotations, and CD spectra.The mechanism of the rearrangement leading to the β-hydroxy and β-chloro acids (S)-11 and (R)-12 is interpreted in terms of a stereospecific 1,2-methyl shift occurring simultaneously with the ring cleavage of the (protonated) α-lactone (R)-2 (R = tBu) which is the crucial intermediate formed in the diazotization of (S)-14.