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

Base Information

Chemical Name: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
CAS No.:848044-31-5
Molecular Formula:C₅₃H₆₂N₂O₉
Molecular Weight:871.083
Hs Code.:

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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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:

: 178977-57-6
tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate

: 848044-30-4
(S)-2-{(R)-3-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid

: 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

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 23 ℃; for 2h;
DOI:10.1002/ejoc.200400558

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

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

: 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

Guidance literature:: Multi-step reaction with 5 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

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