(S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester
• CAS No.: 218927-55-0
• Molecular Formula: C₄₁H₅₂N₄O₁₀
• Molecular Weight: 760.885
• Mol file: 218927-55-0.mol

Synonyms:(S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester

Chemical Property of (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester

There total 5 articles about (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl 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: 50.0%

6-(((benzyloxy)carbonyl)amino)-2-((tert butoxycarbonyl)amino)-hexanoic acid (2389-45-9,55878-47-2,52634-49-8) + (S)-2-Acetylamino-3-[3-((S)-2-amino-2-methoxycarbonyl-ethyl)-phenyl]-propionic acid benzyl ester → (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester (218927-55-0)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1.) 0 deg C, 1 h, 2.) r.t., 16 h;

DOI:10.1039/a805350b

Reference yield:

1-Bromo-3-iodobenzene (591-18-4) → (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester (218927-55-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent / NaHCO₃, Bu₄NCl, hydroquinone / Pd(OAc)2 / dimethylformamide / 18 h / 60 °C

2: 57 percent / NaHCO₃, Bu₄NCl, hydroquinone / Pd(OAc)2 / dimethylformamide / 85 °C

3: 98 percent / H₂ / >⁽¹⁺⁾*OTf^(1-) / methanol / 6 h / 2068.6 Torr / Ambient temperature

4: TFA / 0.25 h / Ambient temperature

5: 50 percent / Et₃N, HOBt*H₂O, DCC / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 16 h

With tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; hydroquinone; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium diacetate; benzene; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1039/a805350b

Reference yield:

(Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester (218927-23-2) → (S)-3-[3-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-phenyl]-2-((S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-propionic acid methyl ester (218927-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 57 percent / NaHCO₃, Bu₄NCl, hydroquinone / Pd(OAc)2 / dimethylformamide / 85 °C

2: 98 percent / H₂ / >⁽¹⁺⁾*OTf^(1-) / methanol / 6 h / 2068.6 Torr / Ambient temperature

3: TFA / 0.25 h / Ambient temperature

4: 50 percent / Et₃N, HOBt*H₂O, DCC / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 16 h

With tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; hydroquinone; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium diacetate; benzene; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1039/a805350b

upstream raw materials:

6-(((benzyloxy)carbonyl)amino)-2-((tert butoxycarbonyl)amino)-hexanoic acid

1-Bromo-3-iodobenzene

(Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester

(Z)-2-Acetylamino-3-[3-((Z)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid benzyl ester

Downstream raw materials:

(S)-2-Acetylamino-3-{3-[(S)-2-((S)-6-amino-2-tert-butoxycarbonylamino-hexanoylamino)-2-methoxycarbonyl-ethyl]-phenyl}-propionic acid