(2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine

Base Information

• Chemical Name: (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine
• CAS No.: 188346-52-3
• Molecular Formula: C₃₉H₅₂N₂O₁₀
• Molecular Weight: 708.849
• Mol file: 188346-52-3.mol

Synonyms:(2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine

Chemical Property of (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine

There total 5 articles about (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine 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: 75.0%

D-4-hydroxyphenylglycine (22818-40-2) + (1S,3E)-5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-1-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-5-oxo-3-pentenyl-(2S)-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoate (188346-51-2) → (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine (188346-52-3)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; In N,N-dimethyl-formamide; at 55 - 60 ℃;

DOI:10.1021/jm980706s

Reference yield:

(5S)-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-8-phenyl-(2E,7E)-octadienoic acid (162465-29-4) → (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine (188346-52-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide / dimethylformamide / 28 h / Ambient temperature

2: 78 percent / 48 percent aq. HF / acetonitrile / 5 h / 0 - 25 °C

3: 79 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.3 h / Ambient temperature

4: 75 percent / N,O-bis(trimethylsilyl)acetamide / dimethylformamide / 55 - 60 °C

With dmap; N,O-bis-(trimethylsilyl)-acetamide; hydrogen fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm980706s

Reference yield:

(5S)-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-8-phenyl-(2E,7E)-octadienoic acid methyl ester (162465-28-3) → (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine (188346-52-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / 1 N aq. LiOH / acetone / 23.5 h / Ambient temperature

2: 80 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide / dimethylformamide / 28 h / Ambient temperature

3: 78 percent / 48 percent aq. HF / acetonitrile / 5 h / 0 - 25 °C

4: 79 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.3 h / Ambient temperature

5: 75 percent / N,O-bis(trimethylsilyl)acetamide / dimethylformamide / 55 - 60 °C

With dmap; lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; hydrogen fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jm980706s

upstream raw materials:

D-4-hydroxyphenylglycine

(1S,3E)-5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-1-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-5-oxo-3-pentenyl-(2S)-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoate

(5S)-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-8-phenyl-(2E,7E)-octadienoic acid

(5S)-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-8-phenyl-(2E,7E)-octadienoic acid methyl ester

Downstream raw materials:

cyclo<2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-(2R)-2-(4-hydroxyphenyl)glycyl>