76549-02-5

Basic information

• Product Name: (2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid
• Synonyms: (2S,3S)-2-Methyl-3-hydroxy-3-phenylpropionic acid;(2S,3S)-2-Methyl-3-phenyl-3-hydroxypropionic acid;(2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid;[2S,3S,(-)]-3-Hydroxy-2-methyl-3-phenylpropanoic acid
• CAS NO: 76549-02-5
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• Mol File: 76549-02-5.mol
• Article Data: 42

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid(76549-02-5)
• EPA Substance Registry System: (2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid(76549-02-5)

Safety Data

• Hazardous Substances Data: 76549-02-5(Hazardous Substances Data)

Usage

Description

(2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid is a chiral molecule with a molecular formula C10H12O3. It is a derivative of phenylpropanoic acid and is commonly found in natural products such as plants and fungi. (2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid has two stereoisomers, which are mirror images of each other, and has been studied for its potential biological activities, including anti-inflammatory and anti-cancer properties.

Uses

Used in Pharmaceutical Industry:
(2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid is used as a precursor for the synthesis of various drugs due to its unique chemical structure and potential biological activities.
Used in Flavor and Fragrance Industry:
(2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid is used as a building block for the production of flavors and fragrances, taking advantage of its natural occurrence and unique chemical properties.
Used in Research and Development:
(2S,3S)-3-Hydroxy-2-methyl-3-phenylpropanoic acid is used in research and development for studying its potential biological activities, such as anti-inflammatory and anti-cancer properties, and exploring its applications in various fields.

Upstream product

• 77877-25-9 (4S)-3-((2S,3S)-3-hydroxy-2-methyl-1-oxo-3-phenylpropyl)-4-(1-methylethyl)-2-oxazolidinone 
• 131701-06-9 (2S,3S)-3-Hydroxy-2-methyl-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-3-phenyl-propan-1-one 
• 132939-79-8 (1S,2S,4S)-1,4-dihydroxy-2,5,5-trimethyl-1-phenyl-3-hexanone 
• 76549-03-6 methyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate 
• 100-52-7 benzaldehyde 
• 76498-61-8 (1R,3S,4S)-4-Hydroxy-3-methyl-4-phenyl-1-((3aR,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-1-trimethylsilanyloxy-butan-2-one 
• 78944-45-3 (2S,3S)-3-Hydroxy-1-((S)-4-isopropyl-oxazolidin-3-yl)-2-methyl-3-phenyl-propan-1-one 
• 145656-33-3 (3aS,8aR)-3-((2S,3S)-3-Hydroxy-2-methyl-3-phenyl-propionyl)-3,3a,8,8a-tetrahydro-indeno[1,2-d]oxazol-2-one 
• 147168-92-1 N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 
• 155323-21-0 C₂₁H₂₇NO₄ 
• 802294-64-0 propionic acid 
• 184583-20-8 (3aR,8bS)-3-((2S,3S)-3-Hydroxy-2-methyl-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one 
• 133467-37-5 (4S)-3-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoyl]-4-benzyl-2-oxazolidinone 
• 461411-91-6 (1S,2R)-(E)-2-methyl-1-phenyl-3-decen-1-ol 

Downstream Products

• 76549-03-6 methyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate 
• 127379-92-4 (1S,2R)-2-methyl-1-phenyl-propane-1,3-diol 
• 16251-45-9 (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one 
• 101450-38-8 (2RS,3SR)-3-hydroxy-2-methyl-3-phenyl-propionic acid-(2-diethylamino-ethyl ester) 
• 17226-79-8 methyl 3-hydroxy-2-methyl-3-phenylpropanoate 
• 116126-02-4 (+)-(2S,3R)-3-hydroxy-2-methyl-3-phenylpropanoic acid 
• 873-66-5 1-propenylbenzene 
• 71155-82-3 3-methyl-4-phenyl-oxetan-2-one 
• 766-90-5 cis-1-phenyl-1-propylene 
• 7087-77-6 (1S,2S) /(1R,2R)-2-methyl-1-phenylpropane-1,3-diol 
• 76943-97-0 (2SR,3RS)-N-(3-hydroxy-2-methyl-3-phenylpropionyl)pyrrolidine 
• 94199-26-5 (2S,3R)-methyl 3-hydroxy-2-methyl-3-phenylpropionate 
• 29478-51-1 (2RS,3SR)-3-hydroxy-2-methyl-3-phenylpropionamide 
• 36393-58-5 anti-3-hydroxy-2-methyl-3-phenylpropanylamine 

Relevant articles and documents

Synthesis and Enantioselective Aldol Reaction of a Chiral 2-Oxo-2-propionyl-1,3,2-oxazaphosphorinane

The synthesis of cis- and trans-2-oxo-2-propionyl-1,3,2-oxazaphosphorinane (cis- and trans-7), via the condensation of (S)-N-isopropyl-4-aminobutan-2-ol (5) with methyl dichlorophosphite (CH3OPCl2), followed by the Michaelis-Arbusov coupling with propionyl chloride is described, and our preliminary research involving metal-directed diastereo- and enantioselective aldol reactions between the lithio enolate of trans-oxazaphosphorinane 7 and benzaldehyde are also discussed.

Siloxy Esters as Traceless Activators of Carboxylic Acids: Boron-Catalyzed Chemoselective Asymmetric Aldol Reaction**

The catalytic asymmetric aldol reaction is among the most useful reactions in organic synthesis. Despite the existence of many prominent reports, however, the late-stage, chemoselective, catalytic, asymmetric aldol reaction of multifunctional substrates is still difficult to achieve. Herein, we identified that in situ pre-conversion of carboxylic acids to siloxy esters facilitated the boron-catalyzed direct aldol reaction, leading to the development of carboxylic acid-selective, catalytic, asymmetric aldol reaction applicable to multifunctional substrates. Combining experimental and computational studies rationalized the reaction mechanism and led to the proposal of Si/B enediolates as the active species. The silyl ester formation facilitated both enolization and catalyst turnover by acidifying the α-proton of substrates and attenuating poisonous Lewis bases to the boron catalyst.

Anti-Selective enolboration-aldolization of propanoic acid

A systematic examination of enolboration-aldolization of propanoic acid has led to an efficient synthesis of anti-β-hydroxy-α-methyl carboxylic acids in consistently high yields and diastereoselectivities by using B-bromodicyclohexylborane as the enolizat