N-Cbz-(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid

Base Information

• Chemical Name: N-Cbz-(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid
• CAS No.: 62023-58-9
• Molecular Formula: C18H19NO5
• Molecular Weight: 329.35
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90456370
• Wikidata: Q82278797
• Mol file: 62023-58-9.mol

Synonyms:62023-58-9;N-Cbz-(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid;Z-(2R,3R)-AHPA;(2R,3R)-2-hydroxy-4-phenyl-3-(phenylmethoxycarbonylamino)butanoic acid;(2R,3R)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoic acid;(2R,3R)-3-{[(BENZYLOXY)CARBONYL]AMINO}-2-HYDROXY-4-PHENYLBUTANOIC ACID;DTXSID90456370;(2R,3R)-3-(benzyloxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid

Chemical Property of N-Cbz-(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid

Chemical Property:

• Melting Point: 172-174 °C
• Boiling Point: 581.9±50.0 °C(Predicted)
• PKA: 3.56±0.17(Predicted)
• PSA: 95.86000
• Density: 1.295±0.06 g/cm3(Predicted)
• LogP: 2.36050
• Storage Temp.: −20°C
• 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

N-CBZ-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC 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 N-Cbz-(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid

There total 4 articles about N-Cbz-(2R,3R)-3-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%

(2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester (124782-06-5) → (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid (62023-58-9,76498-22-1)

Guidance literature:

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

DOI:10.1021/jo00294a047

Reference yield:

N-(benzyloxycarbonyl)-D-phenylalaninal (63219-70-5) → (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid (62023-58-9,76498-22-1)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / 480 h / 20 °C

2: 1.) HCl, 2.) H₂O / 1.) diethyl ether, below 5 deg C, 24h, 2.) below 10 deg C

3: 100 percent / NaOH / dioxane; H₂O / 1 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; water; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/jo00294a047

Reference yield:

((R)-1-Benzyl-2-cyano-2-trimethylsilanyloxy-ethyl)-carbamic acid benzyl ester (144676-39-1,144676-40-4) → (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid (62023-58-9,76498-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HCl, 2.) H₂O / 1.) diethyl ether, below 5 deg C, 24h, 2.) below 10 deg C

2: 100 percent / NaOH / dioxane; H₂O / 1 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; water; In 1,4-dioxane; water;

DOI:10.1021/jo00294a047

upstream raw materials:

potassium cyanide

benzyl chloroformate

[(R)-1-Benzyl-2-(3,5-dimethyl-pyrazol-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

(2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester

Downstream raw materials:

Epibestatin

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

(R)-2-((2R,3R)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid benzyl ester

(S)-2-((2R,3R)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid benzyl ester