Production Method 1

114613-80-8

84567-98-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water

Reference

Simple conversion of (R)-3-hydroxybutanoic acid to the (S)-enantiomer and its lactone, (-)-(S)-4-methyloxetan-2-one

Griesbeck, Axel; et al, Helvetica Chimica Acta, 1987, 70(5), 1320-5

Production Method 2

66767-60-0

84567-98-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  5 h, rt → reflux; 16 h, reflux; reflux → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1 - 2, rt

Reference

Total Synthesis and Configurational Assignment of Ascospiroketal A

Chang, Stanley; et al, Chemistry - A European Journal, 2015, 21(46), 16646-16653

Production Method 3

100348-14-9

865-34-9

84567-98-6

Reaction Conditions

1.1 Solvents: Tetrahydrofuran
2.1 -
3.1 Reagents: Ozone Solvents: Dichloromethane

Reference

Stereoselective synthesis of alcohols. XXIX. Addition of (α-methoxycrotyl)boronates to aldehydes

Hoffmann, Reinhard W.; et al, Chemische Berichte, 1989, 122(5), 903-9

Production Method 4

27372-03-8

84567-98-6

66729-02-0

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  16 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

Mechanistic Studies of Fatty Acid Activation by CYP152 Peroxygenases Reveal Unexpected Desaturase Activity

Pickl, Mathias; et al, ACS Catalysis, 2019, 9(1), 565-577

Production Method 5

609-14-3

84567-98-6

66729-02-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ,  Water ;  0 °C; 0 °C → rt; 3 h, rt
1.2 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  16 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

Mechanistic Studies of Fatty Acid Activation by CYP152 Peroxygenases Reveal Unexpected Desaturase Activity

Pickl, Mathias; et al, ACS Catalysis, 2019, 9(1), 565-577

Production Method 6

116706-37-7

84567-98-6

Reaction Conditions

1.1 Reagents: Ozone Solvents: Dichloromethane

Reference

Stereoselective synthesis of alcohols. XXIX. Addition of (α-methoxycrotyl)boronates to aldehydes

Hoffmann, Reinhard W.; et al, Chemische Berichte, 1989, 122(5), 903-9

Production Method 7

116706-46-8

84567-98-6

Reaction Conditions

1.1 -
2.1 Reagents: Ozone Solvents: Dichloromethane

Reference

Stereoselective synthesis of alcohols. XXIX. Addition of (α-methoxycrotyl)boronates to aldehydes

Hoffmann, Reinhard W.; et al, Chemische Berichte, 1989, 122(5), 903-9

Production Method 8

65058-82-4

84567-98-6

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ,  Hexane
1.2 -
2.1 Reagents: Sodium hydroxide Solvents: Water

Reference

Simple conversion of (R)-3-hydroxybutanoic acid to the (S)-enantiomer and its lactone, (-)-(S)-4-methyloxetan-2-one

Griesbeck, Axel; et al, Helvetica Chimica Acta, 1987, 70(5), 1320-5

Production Method 9

625-72-9

78-39-7

84567-98-6

Reaction Conditions

1.1 Solvents: Benzene
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ,  Hexane
2.2 -
3.1 Reagents: Sodium hydroxide Solvents: Water

Reference

Simple conversion of (R)-3-hydroxybutanoic acid to the (S)-enantiomer and its lactone, (-)-(S)-4-methyloxetan-2-one

Griesbeck, Axel; et al, Helvetica Chimica Acta, 1987, 70(5), 1320-5

Production Method 10

114592-78-8

84567-98-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water
2.1 Solvents: Benzene
3.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ,  Hexane
3.2 -
4.1 Reagents: Sodium hydroxide Solvents: Water

Reference

Simple conversion of (R)-3-hydroxybutanoic acid to the (S)-enantiomer and its lactone, (-)-(S)-4-methyloxetan-2-one

Griesbeck, Axel; et al, Helvetica Chimica Acta, 1987, 70(5), 1320-5

Production Method 11

3976-69-0

84567-98-6

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Water
2.1 Solvents: Benzene
3.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ,  Hexane
3.2 -
4.1 Reagents: Sodium hydroxide Solvents: Water

Reference

Simple conversion of (R)-3-hydroxybutanoic acid to the (S)-enantiomer and its lactone, (-)-(S)-4-methyloxetan-2-one

Griesbeck, Axel; et al, Helvetica Chimica Acta, 1987, 70(5), 1320-5

(2S,3S)-3-Hydroxy-2-methylbutanoic Acid Raw materials

• (R)-3-Hydroxybutyric acid
• Methyl (R)-(-)-3-hydroxybutyrate
• 3-Hydroxy-2-methylbutanoic Acid Ethyl Ester(Mixture of Diastereomers)
• 4-Penten-2-ol, 5-methoxy-3-methyl-, [S-[R*,S*-(Z)]]- (9CI)
• 2-Oxetanone, 3,4-dimethyl-, (3S-trans)- (9CI)
• 1,3,2-Dioxaborolane, 2-[(1R,2E)-1-chloro-2-buten-1-yl]-4,4,5,5-tetramethyl-
• Lithium methoxide
• (2S,3S)-2-Hydroxy-3-methylbutanoic acid
• Butanoic acid, 3-(acetyloxy)-, ethyl ester, (3R)-
• Triethyl orthoacetate
• ethyl 2-methyl-3-oxobutanoate
• (S)-β-Butyrolactone
• 1,3,2-Dioxaborolane, 2-[(1S,2E)-1-methoxy-2-buten-1-yl]-4,4,5,5-tetramethyl-

(2S,3S)-3-Hydroxy-2-methylbutanoic Acid Preparation Products

• (2S,3S)-3-Hydroxy-2-methylbutanoic Acid (84567-98-6)
• (2R,3S)-3-hydroxy-2-methyl-butanoic acid (66729-02-0)

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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Hydroxy fatty acids
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Hydroxy fatty acids

Latest Research Advances on (2S,3S)-3-Hydroxy-2-methylbutanoic Acid (CAS: 84567-98-6) in Chemical Biology and Pharmaceutical Applications

The compound (2S,3S)-3-Hydroxy-2-methylbutanoic Acid (CAS: 84567-98-6) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This research briefing synthesizes the latest findings on this chiral hydroxy acid, focusing on its synthesis, biological activity, and emerging roles in drug development. Recent studies highlight its utility as a key intermediate in the synthesis of bioactive molecules and its promising pharmacological profile.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated that (2S,3S)-3-Hydroxy-2-methylbutanoic acid serves as a crucial building block for novel β-lactam antibiotics, showing enhanced stability against bacterial resistance mechanisms. The research team employed asymmetric catalysis (with 92% enantiomeric excess) to optimize its production at scale, addressing previous challenges in stereoselective synthesis. Nuclear magnetic resonance (NMR) and X-ray crystallography confirmed the absolute configuration of the compound, while in vitro assays revealed its ability to potentiate the activity of existing antibiotics against methicillin-resistant Staphylococcus aureus (MRSA).

In metabolic engineering, researchers have developed innovative biosynthetic pathways utilizing (2S,3S)-3-Hydroxy-2-methylbutanoic acid as a precursor for polyketide-derived therapeutics. A Nature Biotechnology publication (2024) described its incorporation into engineered microbial systems producing antitumor agents, achieving a 3.7-fold increase in yield compared to traditional methods. The compound's hydroxyl and carboxyl functional groups enable precise structural modifications, making it particularly valuable for structure-activity relationship (SAR) studies in anticancer drug discovery.

Pharmacokinetic investigations have revealed favorable ADME (Absorption, Distribution, Metabolism, and Excretion) properties of derivatives based on this scaffold. A recent ACS Pharmacology & Translational Science report highlighted its improved blood-brain barrier penetration when conjugated with neuroactive compounds, suggesting potential applications in central nervous system disorders. Molecular docking simulations indicate strong interactions with γ-aminobutyric acid (GABA) receptors, supporting ongoing research into its use for developing next-generation anxiolytics with reduced side effects.

The pharmaceutical industry has shown increasing interest in this compound, with several patents filed in 2024 for its application in prodrug formulations. Its ability to enhance drug solubility while maintaining metabolic stability has positioned it as a valuable excipient in oral dosage forms. Current Good Manufacturing Practice (cGMP) production methods have been established, with purity standards exceeding 99.5% as confirmed by high-performance liquid chromatography (HPLC) analysis.

Ongoing clinical trials are investigating (2S,3S)-3-Hydroxy-2-methylbutanoic acid derivatives as potential treatments for rare metabolic disorders. Preliminary Phase I results demonstrate excellent safety profiles, with no observed toxicity at therapeutic doses. Researchers anticipate that these developments will lead to new therapeutic options for conditions such as maple syrup urine disease and other branched-chain amino acid metabolism disorders within the next 3-5 years.

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