470-29-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4-Dihydroxy-3,3-dimethylbutanoic acid is utilized as a key intermediate in the production of various pharmaceuticals. Its unique chemical structure allows for the development of drugs targeting specific biological pathways, contributing to the advancement of medicinal chemistry.
Used in Organic Chemistry as a Reagent:
In the field of organic chemistry, 2,4-Dihydroxy-3,3-dimethylbutanoic acid is employed as a reagent for various chemical reactions. Its versatility in forming different chemical bonds and its stability make it a valuable component in the synthesis of complex organic molecules.
Used in the Study and Treatment of Alkaptonuria:
2,4-Dihydroxy-3,3-dimethylbutanoic acid is central to the research and treatment of alkaptonuria. Understanding its role in the disease helps in the development of therapeutic strategies to manage or mitigate the effects of the disorder, such as reducing the accumulation of homogentisic acid in the body.

InChI:InChI=1/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/t4-/m0/s1

Synthetic route

DL-pantolactone → D-(-)-pantolactone + (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With sodium hydroxide In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water	A 82% B n/a

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + hydrogen cyanide (74-90-8) → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
das α-Oxy-β.β-dimethyl-butyrolaceton entsteht durch Verseifung des entstandenen Oxynitrils mit Salzsaeure;

α-oxy-β.β-dimethyl-butyrolactone → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With -base Die Salze entstehen;

DL-α-hydroxy-β.β-dimethyl-γ-butyrolactone → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With sodium hydroxide das Natriumsalz entsteht;
With barium dihydroxide das Bariumsalz entsteht;

hydrogen cyanide (74-90-8) + sodium bisulfite- compound of β-oxy-α,α-dimethyl-propionaldehyde → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
das α-Oxy-β.β-dimethyl-butyrolaceton entsteht durch Verseifung des entstandenen Oxynitrils mit Salzsaeure;

pantolactone (79-50-5) → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With water; sodium hydroxide In water at 30℃; pH=6.7 - 6.9; Enzymatic reaction;

isobutyraldehyde (78-84-2) + Glyoxilic acid (298-12-4) → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
Stage #1: isobutyraldehyde; Glyoxilic acid With triethylamine at 20 - 30℃; for 3h; Stage #2: With 5%-palladium/activated carbon; hydrogen In 1,2-dichloro-ethane at 20 - 25℃; for 4h; Reagent/catalyst; Temperature; Solvent; Autoclave;

2,4-dihydroxy-3,3-dimethylbutanoic acid ethyl ester → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
Stage #1: 2,4-dihydroxy-3,3-dimethylbutanoic acid ethyl ester With water; sodium hydroxide at 100℃; for 1h; Green chemistry; Stage #2: With hydrogenchloride In water pH=3 - 4; Temperature; Green chemistry;	8.1 g

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → pantolactone (79-50-5)

Conditions	Yield
With sulfuric acid at 80 - 85℃; for 3h; Temperature;	98.3%

3-aminobutanoic acid ethyl ester (5303-65-1) + (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → (+/-)-3-pantoylamino-butyric acid

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → L-pantoic acid (1112-32-9)

Conditions	Yield
With water; Quinine das Chininsalz entsteht;

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → D-pantoic acid (1112-33-0)

Conditions	Yield
With water; Quinine durch optische Spaltung;
With ethanol; Quinine durch optische Spaltung;
With pyridine; water; Quinine durch optische Spaltung;

Upstream product

• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 74-90-8 hydrogen cyanide 
• 79-50-5 pantolactone 
• 78-84-2 isobutyraldehyde 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 79-50-5 pantolactone 
• 1112-32-9 L-pantoic acid 

Relevant academic research and scientific papers

Synthetic method of 2, 4-dihydroxyl-3, 3-dimethyl butyric acid

The invention discloses a synthetic method of 2, 4-dihydroxyl-3, 3-dimethyl butyric acid. The synthetic method of 2, 4-dihydroxyl-3, 3-dimethyl butyric acid comprises following steps: 1), isobutyraldehyde and ethyl oxalyl monochloride are subjected to aldol condensation under the effect of RM to generate 3, 3-dimethyl-2, 4-dioxo ethyl butyrate, wherein M is used for representing an alkali metal, and R is used for representing alkyloxy, hydrogen, amino, or alkyl; 2), 3, 3-dimethyl-2, 4-dioxo ethyl butyrate is subjected to reduction reaction to generate 2, 4-dihydroxyl-3, 3-dimethyl ethyl butyrate, and 2, 4-dihydroxyl-3, 3-dimethyl ethyl butyrate is subjected to hydrolysis so as to obtain a target product. According to the synthetic method, isobutyraldehyde and ethyl oxalyl monochloride are adopted as initial raw materials, aldol condensation reaction, reduction reaction, and hydrolysis reaction are adopted to obtain the target product, compared with the prior art, the advantages of the synthetic method are that: no hypertoxic raw material is adopted, operation safety is high, reaction conditions are not server, and operation is simple, and is convenient to control.

Environment-friendly synthesis method of D-calcium pantothenate intermediate D, L-pantoyl lactone

The invention relates to an environment-friendly synthesis method of a D-calcium pantothenate intermediate D, L-pantoyl lactone. According to the method, isobutyraldehyde and glyoxylic acid are utilized to prepare 2-hydroxy-3-methyl-3-formyl butyric acid (II) under the catalytic action of organic alkali in an aldol condensation mode, then catalytic hydrogenation is conducted, 2,4-dyhydroxy-3,3-dimethyl butyric acid (III) is obtained, after the catalyst is filtered out, the filtrate is subjected to lactonization under the acidic condition, and the D, L-pantoyl lactone is obtained. The raw materials used for the method are cheap and easy to obtain, the technological process is short, product cost is low, less wastewater is generated, and treatment is easy to conduct; highly toxic raw materials are avoided, and operation is safe.

A new chemo-enzymatic route to chiral 2-hydroxy-4-phenylbutyrates by combining lactonase-mediated resolution with hydrogenation over Pd/C

A new chemo-enzymatic route to both isomers of 2-hydroxy-4-phenylbutyric acid is reported. The key step is the lactonase-catalyzed hydrolysis of cis- and trans-2-hydroxy-4-phenyl-4-butyrolactones followed by hydrogenation over Pd/C to afford optically pure 2-hydroxy-4-phenylbutyric acid.

Nopinylamines

The nopinylamines of the general formula I STR1 where R1 and R2 are hydrogen or alkyl of 1 to 5 carbon atoms, and the salts of these amines with mineral acids and with alkylcarboxylic acids of 1 to 4 carbon atoms. The manufacture of I from nopinone (II) STR2 by aminating hydrogenation with amines (III) STR3 The use of I for resolving racemates of acid or acid-forming compounds, especially of DL-pantolactone.