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

Base Information

• Chemical Name: Benzoic acid (2E,4Z,7Z)-(S)-16-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester
• CAS No.: 358750-10-4
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.623
• Mol file: 358750-10-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about Benzoic acid (2E,4Z,7Z)-(S)-16-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl 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: 99.0%

Benzoic acid (2E,4Z,7Z)-(S)-16-(tert-butyl-dimethyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester (358750-09-1) → Benzoic acid (2E,4Z,7Z)-(S)-16-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester (358750-10-4)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; at 20 ℃; for 2h;

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

Reference yield:

Methyl 5S-benzoyloxy-5-formylvalerate (76745-20-5) → Benzoic acid (2E,4Z,7Z)-(S)-16-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester (358750-10-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / acetone / 5 h / Heating

2: 56 percent / LiHMDS; HMPA / tetrahydrofuran / -98 - -78 °C

3: 99 percent / DDQ; H₂O / tetrahydrofuran / 2 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; acetone; 2: Wittig reaction;

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) → Benzoic acid (2E,4Z,7Z)-(S)-16-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester (358750-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / LiHMDS; HMPA / tetrahydrofuran / -98 - -78 °C

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

With N,N,N,N,N,N-hexamethylphosphoric triamide; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; 1: Wittig reaction;

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

upstream raw materials:

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

Methyl 5S-benzoyloxy-5-formylvalerate

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

tert-butyl-(12-iodo-dodec-9-enyloxy)-dimethyl-silane

Downstream raw materials:

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

Benzoic acid (2E,4Z,7Z)-(S)-16-(2-azido-5-iodo-benzoylamino)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,7-trienyl ester

Benzoic acid (2E,4Z,7Z)-(S)-16-azido-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