(2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid

Base Information

• Chemical Name: (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid
• CAS No.: 146297-34-9
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• Mol file: 146297-34-9.mol

Synonyms:(2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid

Chemical Property of (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid

There total 6 articles about (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

L-kynurenine (2922-83-0) + benzaldehyde (100-52-7) → (2S,4R)-2-amino-4-hydroxy-4-phenylbutanoic acid (135457-26-0) + (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid (146297-34-9)

Guidance literature:

In water; for 24h; Mechanism; Ambient temperature; Pseudomonas kynureninase, Tris*HCl (pH 8.0), pyridoxal-5'-phosphate;

DOI:10.1021/ja00019a039

Reference yield:

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + benzaldehyde (100-52-7) → L-alanin (56-41-7,25191-17-7,18875-37-1) + (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid (146297-34-9)

Guidance literature:

With pyridoxal 5'-phosphate; UstD from Aspergillus pseudonomius; D,L-dithiothreitol; In aq. phosphate buffer; at 25 ℃; for 72h; pH=7.4; Concentration; Time; diastereoselective reaction; Enzymatic reaction;

DOI:10.1039/d1cy00955a

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid (146297-34-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,2-dichloro-ethane / 6 h / Heating

1.2: Zn / 20 h

2.1: K₂CO₃ / methanol / 1.5 h / Heating

3.1: 99 percent / aq. HCl / tetrahydrofuran / 22 h / Heating

4.1: 105 mg / aq. NaOH / methanol / 0.5 h / 20 °C / pH 10

With hydrogenchloride; sodium hydroxide; potassium carbonate; In tetrahydrofuran; methanol; 1,2-dichloro-ethane;

DOI:10.1021/ol049505a

upstream raw materials:

L-kynurenine

benzaldehyde

styrene

(2R,5S,2'S)-2-tert-butyl-5-(2'-phenyl-2'-hydroxy-ethyl)-3-methylimidazolidin-4-one

Refernces

• 1、 Zhang, Rui,Tan, Jiamu,Luo, Zhenzhen,Dong, Haihong,Ma, Ningshan,Liao, Cangsong. "Stereo-selective synthesis of non-canonical γ-hydroxy-α-amino acids by enzymatic carbon-carbon bond formation". . p. 7380 - 7385. Retrieved 2021/11/27.
• 2、 Miura, Tsuyoshi,Masuo, Noriko,Fusamae, Yuki,Kajimoto, Tetsuya,Ida, Yoshiteru. "Kynureninase in organic synthesis : Preparation of γ-hydroxy-α-L-amino acids". . p. 631 - 633. Retrieved 2007/10/03.