(2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-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-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid
CAS No.:1027848-20-9
Molecular Formula:C₄₉H₅₄N₂O₉
Molecular Weight:814.976
Hs Code.:

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

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

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

There total 13 articles about (2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-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:

: 848044-31-5
tert-butyl (2E,5S,6R,7E)-5-[(2S)-2-{[(2R)-3-({N-[(9H-fluoren-9-yl-methoxy)carbonyl]-D-phenylalanyl}amino)-2-methylpropanoyl]oxy}-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2,7-dienoate

: 1027848-20-9
(2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 23 ℃; for 2h;
DOI:10.1002/ejoc.200400558

Reference yield:

: 86123-10-6
Fmoc-D-Phe-OH

: 1027848-20-9
(2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / HOBt; DCC / tetrahydrofuran / 7 h / 23 °C

2: trifluoroacetic acid / CH₂Cl₂ / 3 h / 23 °C

3: 231 mg / DIEA; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 2 h / 23 °C

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

With dmap; 2,4,6-trichlorobenzoyl chloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.200400558

Reference yield:

: 3069-52-1
(2S)-2-hydroxy-4-methylpentanoic acid 1,1-dimethylethyl ester

: 1027848-20-9
(2E,7E)-(5S,6R)-5-((S)-2-{(R)-3-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 81 percent / HOBt; DCC / tetrahydrofuran / 7 h / 23 °C

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

5: 231 mg / DIEA; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 2 h / 23 °C

6: trifluoroacetic acid / CH₂Cl₂ / 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