Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester

Base Information

• Chemical Name: Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester
• CAS No.: 78606-81-2
• Molecular Formula: C₂₈H₃₈O₅
• Molecular Weight: 454.607
• Mol file: 78606-81-2.mol

Synonyms:Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester

Chemical Property of Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester

There total 13 articles about Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl 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: 65.0%

Methyl 5S-benzoyloxy-5-formylvalerate (76745-20-5) + {(Z)-4-[(2R,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-but-3-enyl}-triphenyl-phosphonium; iodide (78606-77-6) → Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester (78606-81-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1) 1h, -78 deg C, 2) 2.5 h, -78 to 0 deg C;

DOI:10.1016/S0040-4039(01)90241-2

Reference yield:

methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate (78606-78-7) → Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester (78606-81-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / H₂ / Pd-C / ethanol / 25 °C / 760 Torr

2: 75 percent / pyridine / 24 h / 0 °C

3: 96 percent / K₂CO₃ / methanol / 25 °C

4: 96 percent / pyridine / 1 h / 25 °C

5: 80 percent / dimethyl carbonate, 70percent HClO₄ / H₂O

6: lead tetraacetate, Na₂CO₃ / CH₂Cl₂ / 0.17 h / -40 °C

7: 65 percent / n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) 1h, -78 deg C, 2) 2.5 h, -78 to 0 deg C

With lead(IV) acetate; n-butyllithium; perchloric acid; hydrogen; sodium carbonate; potassium carbonate; carbonic acid dimethyl ester; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(01)90241-2

Reference yield:

(2R,3R)-2-((Z)-4-Iodo-but-1-enyl)-3-((Z)-oct-2-enyl)-oxirane → Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester (78606-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 12 h / 60 °C

2: 65 percent / n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) 1h, -78 deg C, 2) 2.5 h, -78 to 0 deg C

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile;

DOI:10.1016/S0040-4039(01)90241-2

upstream raw materials:

Methyl 5S-benzoyloxy-5-formylvalerate

{(Z)-4-[(2R,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-but-3-enyl}-triphenyl-phosphonium; iodide

(Z)-4-[(2R,3R)-((Z)-3-Oct-2-enyl)-oxiranyl]-but-3-en-1-ol

(2R,3R)-2-[(Z)-4-(1-Methoxy-1-methyl-ethoxy)-but-1-enyl]-3-((Z)-oct-2-enyl)-oxirane

Downstream raw materials:

Leukotriene B