Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester
• CAS No.: 80335-91-7
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Mol file: 80335-91-7.mol

Synonyms:Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester

Chemical Property of Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester

There total 1 articles about Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl 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: 90.0%

Methyl 5S-benzoyloxy-5-formylvalerate (76745-20-5) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester (80335-91-7)

Guidance literature:

In benzene; for 2h; Heating;

DOI:10.1016/S0040-4039(01)81899-2

Reference yield: 56.0%

Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester (80335-91-7) + [12-(tert-butyl-dimethyl-silanyloxy)-dodec-3-enyl]-triphenyl-phosphonium; iodide → Benzoic acid (2E,4Z,7Z)-(S)-16-(tert-butyl-dimethyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester (358750-09-1)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -98 - -78 ℃;

DOI:10.1016/S0040-4039(01)00699-2

Reference yield:

Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester (80335-91-7) → (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-hydroxy-icosa-6,8,11-trienoic acid

Guidance literature:

Multi-step reaction with 7 steps

1.1: 56 percent / LiHMDS; HMPA / tetrahydrofuran / -98 - -78 °C

2.1: 99 percent / DDQ; H₂O / tetrahydrofuran / 2 h / 20 °C

3.1: 92 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 0 - 20 °C

4.1: 97 percent / NaN₃ / dimethylsulfoxide / 90 °C

5.1: 75 percent / PPh₃; H₂O / tetrahydrofuran / 6 h / 20 °C

6.1: EDCI; HOBT; NaHCO₃ / acetonitrile; CH₂Cl₂ / 8 h / 20 °C

6.2: NaI; chloroamine-T / tetrahydrofuran; H₂O / pH 7.4

7.1: aq. NaOH / 2 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium azide; water; iodine; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.1: Wittig reaction;

DOI:10.1016/S0040-4039(01)00699-2

upstream raw materials:

Methyl 5S-benzoyloxy-5-formylvalerate

(triphenylphosphoranylidene)acetaldehyde

Downstream raw materials:

Benzoic acid (2E,4Z,6E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester

Benzoic acid (2E,4E,6E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester

Benzoic acid (2E,4Z,7Z)-(S)-16-(tert-butyl-dimethyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester

Benzoic acid (2E,4Z,7Z)-(S)-16-amino-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester