28892-73-1

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-2-methylvaleric acid is used as a therapeutic agent for its potential role in treating various metabolic disorders. Its involvement in the metabolism of leucine and its status as a metabolite of isobutyric acid suggest that it could have beneficial effects on lipid metabolism and insulin sensitivity, making it a promising candidate for the development of treatments for conditions related to these metabolic pathways.
Used in Research Applications:
In the field of scientific research, 3-Hydroxy-2-methylvaleric acid is used as a subject of study to explore its potential as a signaling molecule or a bioactive compound. Understanding its role in cellular processes and its interactions with other biochemical pathways can provide insights into the development of new therapeutic strategies and interventions for metabolic-related diseases.
Used in Nutritional Supplements:
3-Hydroxy-2-methylvaleric acid may also be used in the development of nutritional supplements aimed at supporting healthy lipid metabolism and improving insulin sensitivity. Its presence in supplements could potentially offer benefits to individuals looking to manage their metabolic health through dietary means.

InChI:InChI=1/C6H12O3/c1-3-5(7)4(2)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)

Upstream product

• 1424343-96-3 C₁₁H₁₆O₄ 
• 110793-80-1 (R)-5-But-3-enyl-dihydro-furan-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 10353-53-4 1,2-epoxy-5-hexene 
• 137688-20-1 (R)-2-(but-3-en-1-yl)oxirane 
• 1538-21-2 (3R^*,4R^*)-4-hydroxy-3-methylhexene 
• 119460-80-9 (4SR,5SR)-2,5-dihydroxy-2,4-dimethyl-2-O-trimethylsilylheptan-3-one 
• 123-38-6 propionaldehyde 
• 74-88-4 methyl iodide 
• 137033-02-4 (+/-)-3-hydroxy-2-methylenepentanoic acid 
• 802294-64-0 propionic acid 
• 133181-02-9 3-hydroxy-2-methylene-pentanoic acid methyl ester 
• 615-30-5 3-hydroxyl-2-methylpentanal 
• 121811-29-8 ethyl 2-methyl-3-oxopentanoate 

Downstream Products

• 114607-20-4 1-ethylpropyl (2SR,3RS)-3-hydroxy-2-methylpentanoate 
• 96-22-0 pentan-3-one 
• 115367-79-8 4-Ethyl-3-methyl-oxetan-2-one 
• 105-43-1 3-methylvaleric acid 
• 114607-20-4 2-Methyl-3-hydroxypentanoic acid threo-3-pentyl ester 
• 5145-01-7 3,5-dimethyldihydrofuran-2-one 

Relevant academic research and scientific papers

Process development of halaven: Synthesis of the C14-C35 fragment via iterative nozaki-hiyama-kishi reaction-williamson ether cyclization

Multikilogram manufacturing process of the Halaven C14-C35 fragment is described. The synthesis features convergent assembly of subunits by iterative asymmetric Ni/Cr-mediated coupling executed in fixed equipment. Georg Thieme Verlag Stuttgart - New York.

New synthesis of (±)-sitophilate using carboxylic acid dianion methodology - A stereoselectivity study

A simple two-step synthesis of (±)-sitophilate in has been developed by addition of propanal to the lithium enediolate of propanoic acid and subsequent esterification with 3-pentanol under standard Fischer conditions. Efforts to control the diastereoselectiv-ity to generate the syn isomer are described. A modest degree of asymmetric induction is found using chiral amides as base. Georg Thieme Verlag Stuttgart.

Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis-Hillman adducts. Total synthesis of (±)-sitophilate

We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes.

Asymmetric aldol reactions. A new camphor-derived chiral auxiliary giving highly stereoselective aldol reactions of both lithium and titanium(IV) enolates

A new, conformationally rigid camphor-derived N-propionyloxazolidinone effects asymmetric stereochemical control in syn-selective aldol condensations of the derived lithium and titanium(IV) enolates with a variety of aldehydes. Simple and diastereofacial selectivities of the reaction are high, and diastereomeric purities of the crude aldol adducts can be improved, usually by a single recrystallization, to levels of 98-99% in most cases. The observed facial selectivity is best explained by a transition structure in which intramolecular chelation between the oxazolidinone carbonyl oxygen and the metal induces an enolate π-facial differentiation; the major products observed are those expected from chelation control. Hydrolysis of the exocyclic carbonyl of the aldol adducts led to β-hydroxy-α-methylcarboxylic acids, with recovery of the chiral auxiliary. Consonant double-asymmetric induction with (R)-2-(benzyloxy)propanal gave the product expected from oxazolidinone chelation but nonchelation of the aldehyde benzyloxy group.

A VERSATILE SYNTHESIS OF 3-SUBSTITUTED 5-ALKYL BUTYROLACTONES VIA DYOTROPIC REARRANGEMENT

Substituted acetic acid dianions are convertable to 3,5-disubstituted butyrolactones, employing a dyotropic rearrangement as the key step.

CHIRAL PROPIONATE ENOLATE EQUIVALENTS FOR THE STEREOSELECTIVE SYNTHESIS OF THREO- OR ERYTHRO-α-METHYL-β-HYDROXY ACIDS.

The aluminium and copper enolates derived from (n5-C5H5)Fe(CO)(PPh3)COCH2CH3 are chiral propionate enolate equivalents which on reaction with aldehydes (RCHO, R=Me, Et, iPr, tBu) provide stereoselective sytheses of threo-

Chiral Acetate Enolate Equivalent for the Synthesis of β-Hydroxy Acids

The aluminium enolate derived from (η5-C5H5)Fe(CO)(PPh3)(COMe) undergoes stereoselective aldol condensations with aldehydes to generate β-hydroxy acyl complexes which yield β-hydroxy acids on decomplexation.

ERYTHROSELECTIVITY IN ADDITION OF γ-SUBSTITUTED ALLYLSILANES TO ALDEHYDES IN THE PRESENCE OF TITANIUM CHLORIDE

(E)-Crotyltrimethylsilane and (E)-cinnamyltrimethylsilane were allowed to react with aldehydes (RCHO: t-Bu, i-Pr, Et, Me) in the presence of titanium chloride to give erythro homoallyl alcohols with over 93percent selectivity.Lower erythroselectivity was observed in the reaction of (Z)-allylsilanes.

ACYCLIC STEREOSELECTION-13; ARYL ESTERS: REAGENTS FOR THREO-ALDOLIZATION

Preformed Li enolates of hindered aryl esters condense with aldehydes to give predominantly threo aldols.The method has been explored with esters 3 (DMP propionate), 4 (BHT propionate), 5 (DBHA propionate).DMP propionate reacts with benzaldehyde and α-unbranched aliphatic aldehydes to give threo:erythro ratios of about 6.5:1.However, with α-branched aliphatic aldehydes, ester 3 gives only threo-aldols.BHT propionate and DBHA propionate give only threo-aldols with all aldehydes studied.The DMP aldols may be converted into β-hydroxy acids by simple hydrolysis with KOH in aqueous methanol.BHT aldols cannot be hydrolyzed without retroaldolization.However, these aldols can be reduced to diastereomerically pure 1,3-diols.The DBHA aldols can converted into β-hydroxy acids by a method involving oxidation with ceric ammonium nitrate (CAN) in aqueous acetonitrile.Threo-selectivity is also seen in the condensations of DMP butyrate (15), DBHA butyrate (16), DMP pentenoate (17), and BHT pentenoate (18).The approach has been utilized in a stereoselective synthesis of racemic methyl corynomycolate.