tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

Base Information

• Chemical Name: tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate
• CAS No.: 728032-85-7
• Molecular Formula: C₄₃H₅₉ClN₂O₁₀
• Molecular Weight: 799.402
• Mol file: 728032-85-7.mol

Synonyms:tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

Chemical Property of tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

There total 6 articles about tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-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: 82.0%

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate (178977-57-6) + (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid (728032-83-5) → tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate (728032-85-7)

Guidance literature:

(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid; With dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 2h;

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm030555f

Reference yield:

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate (728032-85-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 76 percent / K₂CO₃; tetrabutylammonium iodide / dimethylformamide / 1.5 h / 20 °C

2.1: 90 percent / DMAP; DCC / CH₂Cl₂ / 19.5 h / 0 - 20 °C

3.1: TFA / CH₂Cl₂ / 3.5 h / 20 °C

4.1: 0.63 g / HOBT; DIEA; DCC / tetrahydrofuran / 16.5 h / 0 - 20 °C

5.1: 98 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

6.1: DIEA; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 2 h / 0 °C

6.2: 82 percent / tetrahydrofuran / 2 h / 20 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm030555f

Reference yield:

benzyl (R)-2-hydroxy-4-methylpentanoate (37755-48-9) → tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate (728032-85-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / DMAP; DCC / CH₂Cl₂ / 19.5 h / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 3.5 h / 20 °C

3.1: 0.63 g / HOBT; DIEA; DCC / tetrahydrofuran / 16.5 h / 0 - 20 °C

4.1: 98 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

5.1: DIEA; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 2 h / 0 °C

5.2: 82 percent / tetrahydrofuran / 2 h / 20 °C

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

DOI:10.1021/jm030555f

upstream raw materials:

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

(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid

(R)-2-hydroxy-4-methylpentanoic acid

benzyl (R)-2-hydroxy-4-methylpentanoate

Downstream raw materials:

6-demethyldesepoxy-3-epicryptophycin-1