3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyric acid

Base Information

• Chemical Name: 3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyric acid
• CAS No.: 62023-60-3
• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 329.353
• DSSTox Substance ID: DTXSID501149052
• Nikkaji Number: J1.137.085C
• Wikidata: Q27097272
• Metabolomics Workbench ID: 151190
• Mol file: 62023-60-3.mol

Synonyms:62023-60-3;Z-(2R,3S)-AHPA;3-BENZYLOXYCARBONYLAMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID;(2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoicacid;(2R,3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid;(2R,3S)-3-(((benzyloxy)carbonyl)aMino)-2-hydroxy-4-phenylbutanoic acid;SCHEMBL7245549;DTXSID501149052;AKOS032961414;DB08041;PD005226;Q27097272;(2R,3S)-3-(Benzyloxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid;(alphaR,betaS)-alpha-Hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]benzenebutanoic acid

Chemical Property of 3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyric acid

Chemical Property:

• 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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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 3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyric acid

There total 13 articles about 3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyric 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%

(2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester (126015-22-3) → (2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid (62023-60-3,76498-22-1)

Guidance literature:

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

DOI:10.1055/s-1989-27367

Reference yield: 92.0%

(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)

Guidance literature:

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

DOI:10.1021/ja00153a008

Reference yield: 35.1%

→ (2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid (62023-60-3,76498-22-1)

Guidance literature:

upstream raw materials:

potassium cyanide

benzyl chloroformate

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

(2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester

Downstream raw materials:

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

1-<(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide

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

(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoyl-(S)-proline methyl ester