(R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester

Base Information

• Chemical Name: (R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester
• CAS No.: 169269-89-0
• Molecular Formula: C₂₈H₃₈N₂O₅
• Molecular Weight: 482.62
• Mol file: 169269-89-0.mol

Synonyms:(R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester

Chemical Property of (R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester

There total 7 articles about (R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester 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: 74.0%

(R)-2-(3-Benzyloxy-propyl)-succinic acid 4-tert-butyl ester (169269-87-8) + L-phenylalanine N-methylamide TFA salt → (R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester (169269-89-0)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at -10 - 20 ℃; for 3h;

DOI:10.1021/jm00014a010

Reference yield:

1 ,5-pentanediol (111-29-5) → (R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester (169269-89-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH, 3.) pyridinium dichromate

2: oxalyl chloride, DMF / CH₂Cl₂ / 0 - 20 °C

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, from -78 deg C to RT

4: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, from -78 deg C to RT

5: 94 percent / H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / Ambient temperature

6: 74 percent / diethyl cyanophosphonate, Et₃N / dimethylformamide / 3 h / -10 - 20 °C

With lithium hydroxide; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; diethyl cyanophosphonate; dihydrogen peroxide; sodium hydride; triethylamine; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00014a010

Reference yield:

5-benzyloxypentanoic acid (64740-39-2) → (R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid tert-butyl ester (169269-89-0)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 0 - 20 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, from -78 deg C to RT

3: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, from -78 deg C to RT

4: 94 percent / H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / Ambient temperature

5: 74 percent / diethyl cyanophosphonate, Et₃N / dimethylformamide / 3 h / -10 - 20 °C

With lithium hydroxide; n-butyllithium; oxalyl dichloride; diethyl cyanophosphonate; dihydrogen peroxide; triethylamine; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00014a010

upstream raw materials:

(R)-2-(3-Benzyloxy-propyl)-succinic acid 4-tert-butyl ester

1 ,5-pentanediol

5-benzyloxypentanoic acid

5-(phenylmethoxy)pentanoic acid chloride

Downstream raw materials:

(R)-6-Benzyloxy-3-((S)-1-methylcarbamoyl-2-phenyl-ethylcarbamoyl)-hexanoic acid