(4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate

Base Information

• Chemical Name: (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate
• CAS No.: 1325235-99-1
• Molecular Formula: C₃₂H₄₈N₂O₅
• Molecular Weight: 540.744
• Mol file: 1325235-99-1.mol

Synonyms:(4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate

Chemical Property of (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate

There total 19 articles about (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate 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: 31.0%

(R)-2-(acetylamino)propanoic acid (19436-52-3) + (S,E)-N-(3-(7-hydroxy-4-methyldeca-3,9-dien-1-yl)-5-methoxyphenyl)non-8-enamide (1325235-75-3) → (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate (1325235-99-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ml200108y

Reference yield:

methyl 3,5-dinitrobenzoate (2702-58-1) → (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate (1325235-99-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: lithium / 0 °C / Inert atmosphere

1.2: Reflux; Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; water / 0 - 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: acetic acid / 1,2-dimethoxyethane / 24 h / 50 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 10 h / 20 °C

7.1: 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

7.2: 1 h / 20 °C / Inert atmosphere

8.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 0 - 20 °C / Inert atmosphere

9.1: acetonitrile / 12 h / Inert atmosphere

10.1: N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Molecular sieve

10.2: 0 - 20 °C / Inert atmosphere

10.3: 0.5 h / 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

12.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; iodine; lithium; sodium hydride; diisobutylaluminium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 10.1: Wittig olefination / 10.2: Wittig olefination / 10.3: Wittig olefination / 12.1: Mitsunobu coupling;

DOI:10.1021/ml200108y

Reference yield:

C10H13NO4 (1325235-67-3) → (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-acetamidopropanoate (1325235-99-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 10 h / 20 °C

2.1: 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: acetonitrile / 12 h / Inert atmosphere

5.1: N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Molecular sieve

5.2: 0 - 20 °C / Inert atmosphere

5.3: 0.5 h / 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; iodine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Wittig olefination / 5.2: Wittig olefination / 5.3: Wittig olefination / 7.1: Mitsunobu coupling;

DOI:10.1021/ml200108y

upstream raw materials:

methyl 3,5-dinitrobenzoate

C₁₀H₁₃NO₄

3-(3-amino-5-methoxyphenyl)propan-1-ol

N-(3-(3-hydroxypropyl)-5-methoxyphenyl)non-8-enamide

Refernces