(2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Base Information

• Chemical Name: (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid
• CAS No.: 182486-27-7
• Molecular Formula: C₃₅H₄₅ClN₂O₈
• Molecular Weight: 657.204
• Mol file: 182486-27-7.mol

Synonyms:

Chemical Property of (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

There total 15 articles about (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic 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:

(2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-3-(3-Chloro-4-methoxy-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid (1027041-92-4) → (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid (182486-27-7)

Guidance literature:

With diethylamine; In tetrahydrofuran; at 23 ℃; for 2h;

DOI:10.1002/ejoc.200400558

Reference yield:

(2S)-2-hydroxy-4-methylpentanoic acid 1,1-dimethylethyl ester (3069-52-1) → (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid (182486-27-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / DCC; DMAP / CH₂Cl₂ / 5.5 h / 0 - 23 °C

2: 67 percent / diethylamine / tetrahydrofuran / 12 h / 0 - 23 °C

3: 84 percent / HOBt; DCC / tetrahydrofuran / 7 h / 23 °C

4: 79 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 23 °C

5: 73 percent / DIEA; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 2 h / 23 °C

6: trifluoroacetic acid / CH₂Cl₂ / 2 h / 23 °C

7: diethylamine / tetrahydrofuran / 2 h / 23 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; benzotriazol-1-ol; diethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.200400558

Reference yield:

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate (178977-57-6) → (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-Amino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid (182486-27-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / DIEA; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 2 h / 23 °C

2: trifluoroacetic acid / CH₂Cl₂ / 2 h / 23 °C

3: diethylamine / tetrahydrofuran / 2 h / 23 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.200400558

upstream raw materials:

(2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-3-(3-Chloro-4-methoxy-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

(2S)-2-hydroxy-4-methylpentanoic acid 1,1-dimethylethyl ester

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate

(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methyl-1-pentanol

Downstream raw materials:

cryptophycin C