(R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl ester

Base Information

• Chemical Name: (R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl ester
• CAS No.: 218621-39-7
• Molecular Formula: C₄₈H₅₈F₅N₃O₄
• Molecular Weight: 835.998

Synonyms:

Chemical Property of (R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl ester

Chemical Property:

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Useful:

Technology Process of (R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl ester

There total 6 articles about (R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl 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:

2,3,4,5,6-pentafluorophenol (771-61-9) → (R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl ester (218621-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

2: CF₃COOH / 1 h

With dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/hlca.19970800716

Reference yield:

Boc-Phe-Phe-OH (13122-90-2) → (R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl ester (218621-39-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Et₃N, diethyl phosphorocyanidate / dimethylformamide / 48 h / Ambient temperature

2: 1N aq.NaOH / ethanol / 5 h

3: dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

4: CF₃COOH / 1 h

With sodium hydroxide; diethyl cyanophosphonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19970800716

Reference yield:

(R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-Amino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester; hydrochloride → (R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid pentafluorophenyl ester (218621-39-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Et₃N, diethyl phosphorocyanidate / dimethylformamide / 48 h / Ambient temperature

2: 1N aq.NaOH / ethanol / 5 h

3: dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

4: CF₃COOH / 1 h

With sodium hydroxide; diethyl cyanophosphonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19970800716

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Boc-Phe-Phe-OH

(R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester

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