(2S,3S)-3-(Z-amino)-2-hydroxy-4-phenylbutyric acid

Base Information

• Chemical Name: (2S,3S)-3-(Z-amino)-2-hydroxy-4-phenylbutyric acid
• CAS No.: 62023-59-0
• Molecular Formula: C18H19NO5
• Molecular Weight: 329.353
• DSSTox Substance ID: DTXSID00376737
• Nikkaji Number: J961.752C
• Wikidata: Q82165649
• Mol file: 62023-59-0.mol

Synonyms:62023-59-0;(2S,3S)-3-(Z-amino)-2-hydroxy-4-phenylbutyric acid;(2S,3S)-2-hydroxy-4-phenyl-3-(phenylmethoxycarbonylamino)butanoic acid;Z-(2S,3S)-AHPA;(2S,3S)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoic acid;Benzenebutanoicacid,a-hydroxy-b-[[(phenylmethoxy)carbonyl]amino]-,(as,bs)-;(2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid;starbld0005534;SCHEMBL7418088;DTXSID00376737;JXJYTERRLRAUSF-HOTGVXAUSA-N;(2S,3S)-2-Hydroxy-3-(benzyloxycarbonylamino)-4-phenylbutyric acid;(2S,3S)-3-[(benzyloxycarbonyl) amino]-2-hydroxy-4-phenylbutanoic acid

Chemical Property of (2S,3S)-3-(Z-amino)-2-hydroxy-4-phenylbutyric acid

Chemical Property:

• Vapor Pressure: 2.21E-14mmHg at 25°C
• Refractive Index: 1.602
• Boiling Point: 581.9 °C at 760 mmHg
• PKA: 3.56±0.17(Predicted)
• Flash Point: 305.7 °C
• PSA: 95.86000
• Density: 1.295 g/cm³
• LogP: 2.36050
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 329.12632271
• Heavy Atom Count: 24
• Complexity: 402

Purity/Quality:

99.5% ^*data from raw suppliers

(2S,3S)-3-(Z-AMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID 95.00% ^*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)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H]([C@@H](C(=O)O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (2S,3S)-3-(Z-amino)-2-hydroxy-4-phenylbutyric acid

There total 14 articles about (2S,3S)-3-(Z-amino)-2-hydroxy-4-phenylbutyric 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: 100.0%

(2S,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester (126015-23-4) → (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-59-0,76498-22-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 1h; Ambient temperature;

DOI:10.1055/s-1989-27367

Reference yield: 92.0%

(2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester (172696-23-0) → (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-59-0,76498-22-1)

Guidance literature:

With lithium hydroxide; In methanol; water; for 0.5h; Ambient temperature;

DOI:10.1021/ja00153a008

Reference yield:

(2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester (172696-23-0) + (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester (172696-22-9) → (2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid (62023-60-3,76498-22-1) + (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-59-0,76498-22-1)

Guidance literature:

(2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester; (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester; With lithium hydroxide; water; In methanol; at 20 ℃; for 0.5h;

With hydrogenchloride; In methanol; water; pH=2.0 - 7.0;

upstream raw materials:

potassium cyanide

benzyl chloroformate

(S)-1-(2'-benzyloxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole

allophenylnorstatine

Downstream raw materials:

Z-(2S,3S)-AHPA-(R)-Leu-OBzl

allophenylnorstatine

[(1S,2S)-1-Benzyl-3-((2S,3R,4R,5R)-3,4-dimethoxy-2,5-bis-methoxymethyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid benzyl ester

(2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide