(S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester
• CAS No.: 182742-38-7
• Molecular Formula: C₃₈H₅₄N₄O₈
• Molecular Weight: 694.869

Synonyms:(S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester

Chemical Property of (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester

There total 11 articles about (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric 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: 81.8%

(S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester (1062494-29-4) → (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester (182742-38-7)

Guidance literature:

With pyridinium trifluroacetate; dicyclohexyl-carbodiimide; In dimethyl sulfoxide; benzene; for 6.5h; Ambient temperature;

DOI:10.7164/antibiotics.49.890

Reference yield:

Z-D-Leu-OH (28862-79-5) → (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester (182742-38-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 87.9 percent / HOBt, Et₃N, EDC perchlorate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) room temperature, 15 h

2: 1.1 g / H₂ / palladium-black / methanol / 16 h / Ambient temperature

3: 98 percent / HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 6 h

4: 247.1 mg / H₂ / palladium-black / methanol / 26.5 h / Ambient temperature

5: 99.7 percent / HOBt, EDC*HCl / dimethylformamide / 6 h / 0 °C

6: 81.8 percent / pyridinium trifluoroacetate, DCC / dimethylsulfoxide; benzene / 6.5 h / Ambient temperature

With hydrogen; pyridinium trifluroacetate; benzotriazol-1-ol; 1-ethyl-3-(3-(dimethylammonio)propyl)carbodiimide perchlorate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.7164/antibiotics.49.890

Reference yield:

L-valine tert-butylester hydrochloride (13518-40-6) → (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester (182742-38-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 87.9 percent / HOBt, Et₃N, EDC perchlorate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) room temperature, 15 h

2: 1.1 g / H₂ / palladium-black / methanol / 16 h / Ambient temperature

3: 98 percent / HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 6 h

4: 247.1 mg / H₂ / palladium-black / methanol / 26.5 h / Ambient temperature

5: 99.7 percent / HOBt, EDC*HCl / dimethylformamide / 6 h / 0 °C

6: 81.8 percent / pyridinium trifluoroacetate, DCC / dimethylsulfoxide; benzene / 6.5 h / Ambient temperature

With hydrogen; pyridinium trifluroacetate; benzotriazol-1-ol; 1-ethyl-3-(3-(dimethylammonio)propyl)carbodiimide perchlorate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.7164/antibiotics.49.890

upstream raw materials:

(S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester

Z-D-Leu-OH

Z-homophenylalanine

L-valine tert-butylester hydrochloride

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