(3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid

Base Information

• Chemical Name: (3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid
• CAS No.: 273215-70-6
• Molecular Formula: C₂₉H₄₀N₄O₁₁
• Molecular Weight: 620.657
• Mol file: 273215-70-6.mol

Synonyms:(3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid

Chemical Property of (3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid

There total 9 articles about (3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid 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: 65.0%

(S)-3-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-methyl-butyrylamino}-4-oxo-7-phenyl-heptanoic acid methyl ester (863667-24-7) → (3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid (273215-70-6)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 1.5h;

DOI:10.1021/ol051287d

Reference yield:

Ac-Asp(O-t-Bu)-Glu(O-t-Bu)-Val-OH (263859-12-7) → (3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid (273215-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / PyBOP; DIEA / CH₂Cl₂ / 20 °C

2: 65 percent / KOH / methanol / 1.5 h / 20 °C

With potassium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/ol051287d

Reference yield:

Glu(O-tBu)-Val-Oallyl → (3S)-3-((2S)-2-[((2S)-2-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-4-carboxybutanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid (273215-70-6)

Guidance literature:

Multi-step reaction with 4 steps

1: PyBOP; DIEA / CH₂Cl₂ / 20 °C

2: 94 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.33 h / 20 °C

3: 65 percent / PyBOP; DIEA / CH₂Cl₂ / 20 °C

4: 65 percent / KOH / methanol / 1.5 h / 20 °C

With morpholine; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol051287d

upstream raw materials:

(S)-3-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-methyl-butyrylamino}-4-oxo-7-phenyl-heptanoic acid methyl ester

N-Acetylimidazole

Fmoc-Val-OH

Fmoc-(tBu)Asp-OH

Downstream raw materials:

(3S)-3-((2S)-2-[((2S)-2-[(2R)-2-(Acetylamino)-3-(methylsulfanyl)propanoyl]aminopropanoyl)amino]-3-methylbutanoylamino)-4-oxo-7-phenylheptanoic acid