(11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester

Base Information

• Chemical Name: (11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester
• CAS No.: 205380-53-6
• Molecular Formula: C₂₆H₃₅NO₇
• Molecular Weight: 473.566

Synonyms:(11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester

Chemical Property of (11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester

There total 16 articles about (11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-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: 85.0%

(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9-15-dienoic acid methyl ester + 4-nitro-benzoic acid (62-23-7) → (11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester (205380-53-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at -20 ℃; for 1h;

Reference yield:

(Z)-3-Hexen-1-ol (928-96-1) → (11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester (205380-53-6)

Guidance literature:

Multi-step reaction with 16 steps

1: Dess-Martin periodinane oxidn.

2: n-BuLi / tetrahydrofuran / 0 °C

3: diisobutylaluminum hydride / tetrahydrofuran / 0 °C

4: Dess-Martin periodinane oxidn.

5: 83 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -40 °C

6: pyridine / CH₂Cl₂

7: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

8: Dess-Martin periodinane oxidn.

9: sodium chlorite, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

10: potassium carbonate / dimethylformamide / Ambient temperature

11: potassium carbonate, MeOH / Ambient temperature

12: imidazole / CH₂Cl₂ / Ambient temperature

13: H₂, pyridine / Pd/CaCO₃ / hexane / Ambient temperature

14: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

15: L-(+)-DIPT, tert-butyl hydroperoxide, Ti(Oi-Pr)4, calcium hydride, molecular sieves 3A / CH₂Cl₂ / -40 °C

16: DEAD, Ph₃P / toluene / -20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; calcium hydride; 2-methyl-but-2-ene; L-(+)-diisopropyl tartrate; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.3987/COM-97-S48

Reference yield:

(3Z)-hexenal (6789-80-6) → (11R,12S,13S)-(9Z,15Z)-11-(p-Nitrobenzoyloxy)-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester (205380-53-6)

Guidance literature:

Multi-step reaction with 15 steps

1: n-BuLi / tetrahydrofuran / 0 °C

2: diisobutylaluminum hydride / tetrahydrofuran / 0 °C

3: Dess-Martin periodinane oxidn.

4: 83 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -40 °C

5: pyridine / CH₂Cl₂

6: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

7: Dess-Martin periodinane oxidn.

8: sodium chlorite, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

9: potassium carbonate / dimethylformamide / Ambient temperature

10: potassium carbonate, MeOH / Ambient temperature

11: imidazole / CH₂Cl₂ / Ambient temperature

12: H₂, pyridine / Pd/CaCO₃ / hexane / Ambient temperature

13: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

14: L-(+)-DIPT, tert-butyl hydroperoxide, Ti(Oi-Pr)4, calcium hydride, molecular sieves 3A / CH₂Cl₂ / -40 °C

15: DEAD, Ph₃P / toluene / -20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; calcium hydride; 2-methyl-but-2-ene; L-(+)-diisopropyl tartrate; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.3987/COM-97-S48

upstream raw materials:

4-nitro-benzoic acid

(Z)-3-Hexen-1-ol

(3Z)-hexenal

(2E,5Z)-Octa-2,5-dien-1-ol

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