(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate)

Base Information

• Chemical Name: (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate)
• CAS No.: 1313514-76-9
• Molecular Formula: C₃₉H₅₂N₂O₄
• Molecular Weight: 612.853

Synonyms:(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate)

Chemical Property of (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate)

Chemical Property:

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Technology Process of (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate)

There total 3 articles about (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate) 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: 85.0%

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (2S)-3-(4-benzoylphenyl)-2-[(tert-butoxycarbonyl)amino]propanoate (1313514-75-8) → (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate) (1313514-76-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm2004392

Reference yield:

methanandamide (157182-49-5,157182-50-8) → (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate) (1313514-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 10 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm2004392

Reference yield:

N-tert-butoxycarbonyl-(S)-3-(4-benzoylphenyl)alanine (104504-43-0) → (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate) (1313514-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 10 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm2004392

upstream raw materials:

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (2S)-3-(4-benzoylphenyl)-2-[(tert-butoxycarbonyl)amino]propanoate

methanandamide

N-tert-butoxycarbonyl-(S)-3-(4-benzoylphenyl)alanine

Downstream raw materials:

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} 4-benzoyl-N-(5-hexynoyl)-L-phenylalaninate

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