(2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester

Base Information

• Chemical Name: (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester
• CAS No.: 473980-91-5
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317
• Mol file: 473980-91-5.mol

Synonyms:(2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester

Chemical Property of (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester

There total 3 articles about (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl 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: 91.0%

acetic anhydride (108-24-7) + (2Z,5E)-(S)-7-Hydroxy-7-phenyl-hepta-2,5-dienoic acid methyl ester (473980-85-7) → (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester (473980-91-5)

Guidance literature:

With dmap; triethylamine; at 0 ℃; for 1h;

DOI:10.1055/s-2002-32977

Reference yield:

(1R,2R)-1-phenyl-but-3-ene-1,2-diol (145376-17-6) → (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester (473980-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 71 percent / PdCl₂(CH₃CN)2 / dimethylformamide; H₂O / 1 h / 0 °C

3: 91 percent / Et₃N; DMAP / 1 h / 0 °C

With dmap; triethylamine; dichloro bis(acetonitrile) palladium(II); In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-2002-32977

Reference yield:

(4R,5R)-4-Phenyl-5-vinyl-[1,3]dioxolan-2-one (474087-63-3) → (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester (473980-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / PdCl₂(CH₃CN)2 / dimethylformamide; H₂O / 1 h / 0 °C

2: 91 percent / Et₃N; DMAP / 1 h / 0 °C

With dmap; triethylamine; dichloro bis(acetonitrile) palladium(II); In water; N,N-dimethyl-formamide;

DOI:10.1055/s-2002-32977

upstream raw materials:

acetic anhydride

(2Z,5E)-(S)-7-Hydroxy-7-phenyl-hepta-2,5-dienoic acid methyl ester

(1R,2R)-1-phenyl-but-3-ene-1,2-diol

(4R,5R)-4-Phenyl-5-vinyl-[1,3]dioxolan-2-one

Downstream raw materials:

(Z)-(5R,6S,7R)-7-Acetoxy-5,6-dihydroxy-7-phenyl-hept-2-enoic acid methyl ester

(6R,7R,8R)-goniodiol-8-monoacetate

7,8-di-O-acetyl-goniodiol