(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Base Information

• Chemical Name: (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid
• CAS No.: 59554-14-2
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID50974964
• Nikkaji Number: J35.767G
• Wikidata: Q27447197
• ChEMBL ID: CHEMBL70899
• Mol file: 59554-14-2.mol

Synonyms:59554-14-2;(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid;(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid;(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid;76647-67-1;(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyricacid;beta-Amino-alpha-hydroxybenzenebutanoic acid;CHEMBL70899;(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoic acid;SCHEMBL2029167;DTXSID50974964;MFCD00070368;AKOS006346210;AC-6924;DS-14364;CS-0162360;syn-3-amino-2-hydroxy-4-phenylbutanoic acid;W18729;EN300-4254183;(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyricacid;A832362;A917402;Q27447197;01B

Chemical Property of (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 235-237 °C (decomp)
• Refractive Index: 1.595
• Boiling Point: 428.5 °C at 760 mmHg
• PKA: 2.97±0.17(Predicted)
• Flash Point: 213 °C
• PSA: 83.55000
• Density: 1.285 g/cm³
• LogP: 0.70220
• Storage Temp.: 2-8°C
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 190

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoicAcid ^*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(C(=O)O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)C[C@H]([C@@H](C(=O)O)O)N
• Uses: (2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoic acid is a component of a renin inhibitor and bestatin.

Technology Process of (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

There total 57 articles about (2S,3R)-3-amino-2-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: 85.0%

(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid isopropyl ester (130115-05-8) → (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid (59554-14-2)

Guidance literature:

With hydrogenchloride; ion exchange resin (H+); 1.) 4 h, 100 deg C;

DOI:10.1016/S0040-4039(00)89018-8

Reference yield: 82.0%

(2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoic acid (180922-44-5) → (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid (59554-14-2)

Guidance literature:

With Na-naphthalide; In 1,2-dimethoxyethane; at -78 ℃; for 0.5h;

DOI:10.1002/hlca.19960790426

Reference yield:

(2S,3R)-3-azido-2-hydroxy-4-phenylbutanoic acid (121445-52-1) → (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid (59554-14-2)

Guidance literature:

With sodium tetrahydroborate; copper(II) nitrate; In water; at 0 ℃; for 0.5h;

DOI:10.1021/jo034752y

upstream raw materials:

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid

(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid isopropyl ester

methyl (4R,5S)-2-oxo-4-phenylmethyl-1,3-oxazolidine-5-carboxylate

(2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoic acid

Downstream raw materials:

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid

(2S)-2-[[(2S,3R)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid

methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate

methyl (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoate

Refernces

• 1、 Feske, Brent D.,Stewart, Jon D.. "Chemoenzymatic formal total synthesis of (-)-bestatin". . p. 3124 - 3127. Retrieved 2007/10/03.
• 2、 Fringuelli, Francesco,Pizzo, Ferdinando,Rucci, Mauro,Vaccaro, Luigi. "First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines". . p. 7041 - 7045. Retrieved 2007/10/03.