8S,9R-epoxyeicosatrienoic acid

Base Information

• Chemical Name: 8S,9R-epoxyeicosatrienoic acid
• CAS No.: 123931-39-5
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• Mol file: 123931-39-5.mol

Synonyms:

Chemical Property of 8S,9R-epoxyeicosatrienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8S,9R-epoxyeicosatrienoic acid

There total 6 articles about 8S,9R-epoxyeicosatrienoic acid 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:

8(S),9(R)-epoxyeicosatrienoic acid methyl ester (110901-55-8,132072-50-5) → 8S,9R-epoxyeicosatrienoic acid (123931-39-5,81246-85-7)

Guidance literature:

With sodium hydroxide; In methanol; water;

DOI:10.1016/S0040-4039(00)85391-5

Reference yield:

7-carbomethoxy hepta-3-(Z)-en-1-ylidenetriphenylphosphorane (109296-17-5) → 8S,9R-epoxyeicosatrienoic acid (123931-39-5,81246-85-7)

Guidance literature:

Multi-step reaction with 5 steps

2: t-BuOOH, VO(acac)2 / CH₂Cl₂ / 10 h / 0 °C

3: 1.) KHCO₃ 2.) NaIO₄, Na₂HPO₄ / 1.) methanol, 25 gradC, 10 h 2.) MeOH, H₂O

4: tetrahydrofuran; toluene / 4 h / -100 gradC to -15 gradC

5: NaOH / methanol; H₂O

With tert.-butylhydroperoxide; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; bis(acetylacetonate)oxovanadium; potassium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/S0040-4039(00)85391-5

Reference yield:

Benzoic acid (4Z,7Z)-(S)-2-hydroxy-11-methoxycarbonyl-undeca-4,7-dienyl ester (110822-71-4) → 8S,9R-epoxyeicosatrienoic acid (123931-39-5,81246-85-7)

Guidance literature:

Multi-step reaction with 4 steps

1: t-BuOOH, VO(acac)2 / CH₂Cl₂ / 10 h / 0 °C

2: 1.) KHCO₃ 2.) NaIO₄, Na₂HPO₄ / 1.) methanol, 25 gradC, 10 h 2.) MeOH, H₂O

3: tetrahydrofuran; toluene / 4 h / -100 gradC to -15 gradC

4: NaOH / methanol; H₂O

With tert.-butylhydroperoxide; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; bis(acetylacetonate)oxovanadium; potassium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/S0040-4039(00)85391-5

upstream raw materials:

8(S),9(R)-epoxyeicosatrienoic acid methyl ester

7-carbomethoxy hepta-3-(Z)-en-1-ylidenetriphenylphosphorane

Benzoic acid (4Z,7Z)-(S)-2-hydroxy-11-methoxycarbonyl-undeca-4,7-dienyl ester

Benzoic acid (S)-2-hydroxy-3-[(2R,3S)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-oxiranyl]-propyl ester

Refernces