N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester
• CAS No.: 82652-97-9
• Molecular Formula: C₃₈H₅₀BrN₅O₁₂S
• Molecular Weight: 880.811

Synonyms:N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester

Chemical Property of N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester

There total 6 articles about N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl 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: 94.0%

L-N-Boc-Ala (15761-38-3) + (S)-2-[(R)-3-(Acetylamino-methylsulfanyl)-2-amino-propionylamino]-3-methyl-butyric acid (R)-2-benzyloxycarbonylamino-2-[2-(4-bromo-phenyl)-2-oxo-ethoxycarbonyl]-ethyl ester → N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester (82652-97-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1.) 0 deg C, 1h, 2.) room temperature, 5h;

DOI:10.1016/0040-4020(82)85045-X

Reference yield:

t-Boc-L-valine (13734-41-3) → N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester (82652-97-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / N,N'-dicyclohexylcarbodiimide / pyridine / 1.) 0 deg C, 4 h, 2.) room temperature, 16 h

2: 96 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 87 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.HCl, 1-hydroxybenzotriazole / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 5 h

4: 98 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 94 percent / 1-hydroxybenzotriazole, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.HCl / tetrahydrofuran / 1.) 0 deg C, 1h, 2.) room temperature, 5h

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1016/0040-4020(82)85045-X

Reference yield:

N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine (19746-37-3) → N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine p-bromophenacyl ester (82652-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.HCl, 1-hydroxybenzotriazole / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 5 h

2: 98 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 94 percent / 1-hydroxybenzotriazole, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.HCl / tetrahydrofuran / 1.) 0 deg C, 1h, 2.) room temperature, 5h

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4020(82)85045-X

upstream raw materials:

L-N-Boc-Ala

t-Boc-L-valine

N-t-butoxycarbonyl-S-acetamidomethyl-L-cysteine

N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-valyl)-D-serine p-bromophenacyl ester

Downstream raw materials:

N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine

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