[(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester
• CAS No.: 246870-29-1
• Molecular Formula: C₃₈H₅₀N₄O₆S
• Molecular Weight: 690.904
• Mol file: 246870-29-1.mol

Synonyms:[(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester

Chemical Property of [(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester

There total 8 articles about [(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl 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: 37.0%

2-benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyric acid (246870-25-7) + H2N-L-Lys(ε-Cbz)-CONHCH2Ph (246869-37-4) → [(S)-5-((R)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester (246870-30-4) + [(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester (246870-29-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4020(99)00561-X

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester (246870-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / Et₃N / tetrahydrofuran / 6 h / 20 °C

2: 82 percent / aq. NaOH / dioxane / 5 h / Heating

3: 29 percent / HOBT; EDCI / CH₂Cl₂ / 20 °C

With sodium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Acylation / 2: Hydrolysis / 3: Condensation;

DOI:10.1016/S0040-4020(99)00561-X

Reference yield:

Boc-Lys(Z)-OH (2389-45-9) → [(S)-5-((S)-2-Benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester (246870-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HOBT; EDCI / 12 h / 20 °C

1.2: 66 percent / CF₃COOH / CHCl₃ / 12 h / 20 °C

2.1: 29 percent / HOBT; EDCI / CH₂Cl₂ / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; 1.1: Condensation / 1.2: Hydrolysis / 2.1: Condensation;

DOI:10.1016/S0040-4020(99)00561-X

upstream raw materials:

2-benzyl-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyric acid

H2N-L-Lys(ε-Cbz)-CONHCH2Ph

di-tert-butyl dicarbonate

Boc-Lys(Z)-OH

Downstream raw materials:

[(S)-5-((S)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-5-benzylcarbamoyl-pentyl]-carbamic acid benzyl ester

[(S)-3-Benzyl-1-((S)-1-benzylcarbamoyl-5-benzyloxycarbonylamino-pentyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

{(S)-5-Benzylcarbamoyl-5-[(S)-3-benzyl-3-(3,3-diphenyl-propionylamino)-2-oxo-pyrrolidin-1-yl]-pentyl}-carbamic acid benzyl ester