(3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid

Base Information

• Chemical Name: (3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid
• CAS No.: 72155-50-1
• Molecular Formula: C11H15 N O3
• Molecular Weight: 209.24
• DSSTox Substance ID: DTXSID30472170
• Nikkaji Number: J703.709K
• Wikidata: Q27464557
• Mol file: 72155-50-1.mol

Synonyms:(3S,4S)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID;72155-50-1;L-threo-Pentonic acid,4-amino-2,4,5-trideoxy-5-phenyl-;3-HYDROXY-4-AMINO-5-PHENYLPENTANOIC ACID;(3S,4S)-Ahppa-OH;SCHEMBL3495957;DTXSID30472170;MFCD00153478;AKOS027340105;CS-0208729;EN300-312400;Q27464557;4-amino-2,4,5-trideoxy-5-phenyl-L-threo-pentonic acid

Chemical Property of (3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid

Chemical Property:

• Melting Point: 97 °C
• Boiling Point: 452.0±45.0 °C(Predicted)
• PKA: 3.94±0.10(Predicted)
• PSA: 83.55000
• Density: 1.243±0.06 g/cm3(Predicted)
• LogP: 1.09230
• Storage Temp.: Store at 0-5°C
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 202

Purity/Quality:

99%min ^*data from raw suppliers

(3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(CC(=O)O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H]([C@H](CC(=O)O)O)N

Technology Process of (3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid

There total 27 articles about (3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic 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: 99.0%

(3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid (390377-67-0) → (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid (72155-50-1,153061-61-1)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In methanol; water; for 22h;

DOI:10.1016/S0040-4020(01)00804-3

Reference yield: 80.0%

(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid (72155-48-7) → (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid (72155-50-1,153061-61-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 0.5h; Ambient temperature;

DOI:10.1021/jm00175a006

Reference yield: 73.0%

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate (133333-27-4) → (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid (72155-50-1,153061-61-1)

Guidance literature:

With hydrogenchloride; at 80 ℃;

DOI:10.1016/j.tetlet.2004.05.057

upstream raw materials:

(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid

methyl (4S,5S)-4-benzyl-2-oxooxazolidine-5-acetate

(3S,4S)-3-hydroxy-5-phenyl-4-(N-tosylamino)pentanoic acid

(+)-(4S,5S)-5-benzyl-4-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]-2-pyrrolidinone

Downstream raw materials:

(3S,4S)-4-amino-1-((3R)-3-(1-(3-fluorophenyl)-1-hydroxy-5-methoxypentyl)piperidin-1-yl)-3-hydroxy-5-phenylpentan-1-one

(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid

2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid

Refernces

• 1、 Kondekar, Nagendra B.,Kandula, Subba Rao V.,Kumar, Pradeep. "Application of the asymmetric aminohydroxylation reaction for the syntheses of HIV-protease inhibitor, hydroxyethylene dipeptide isostere and γ-amino acid derivative". . p. 5477 - 5479. Retrieved 2007/10/03.
• 2、 Andrés, José M,Pedrosa, Rafael,Pérez, Alberto,Pérez-Encabo, Alfonso. "Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes". . p. 8521 - 8530. Retrieved 2007/10/03.