(2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid

Base Information

• Chemical Name: (2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid
• CAS No.: 161510-68-5
• Molecular Formula: C₂₃H₃₀N₂O₅
• Molecular Weight: 414.502
• Mol file: 161510-68-5.mol

Synonyms:(2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid

Chemical Property of (2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid

There total 10 articles about (2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-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: 92.0%

(2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid ethyl ester (161510-66-3) → (2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid (161510-68-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 10h; Ambient temperature;

DOI:10.1021/jm00045a013

Reference yield:

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate (124818-94-6,116246-06-1) → (2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid (161510-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / m-CPBA / CH₂Cl₂ / 120 h

2: 87.5 percent / ethanol / 72 h / 60 °C

3: aq. NaOH / tetrahydrofuran / 10 h / 20 °C

With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.bmcl.2006.11.020

Reference yield:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → (2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid (161510-68-5)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine*SO₃; triethylamine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 20 °C

2: 89 percent / toluene / 1 h / 80 °C

3: 91 percent / m-CPBA / CH₂Cl₂ / 120 h

4: 87.5 percent / ethanol / 72 h / 60 °C

5: aq. NaOH / tetrahydrofuran / 10 h / 20 °C

With sodium hydroxide; sulfur trioxide pyridine complex; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; toluene; 2: Wittig reaction;

DOI:10.1016/j.bmcl.2006.11.020

upstream raw materials:

(2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid ethyl ester

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

Downstream raw materials:

[(S)-1-[(1S,2R,3R)-1-Benzyl-3-benzylamino-3-((S)-1-benzylcarbamoyl-2-methyl-propylcarbamoyl)-2-hydroxy-propylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid benzyl ester

(2R,3R,4S)-4-{(S)-2-[3-(1H-Benzoimidazol-2-ylmethyl)-3-methyl-ureido]-3-methyl-butyrylamino}-2-benzylamino-3-hydroxy-5-phenyl-pentanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)-amide

SDZ 283365

SDZ 282395