methyl (4Z,7S,8R,9E,11E,13Z,15E,17R,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate

Base Information

• Chemical Name: methyl (4Z,7S,8R,9E,11E,13Z,15E,17R,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate
• CAS No.: 937738-64-2
• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.52

Synonyms:

Chemical Property of methyl (4Z,7S,8R,9E,11E,13Z,15E,17R,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4Z,7S,8R,9E,11E,13Z,15E,17R,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate

There total 36 articles about methyl (4Z,7S,8R,9E,11E,13Z,15E,17R,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate 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: 93.0%

methyl (4Z,7S,8R,9E,11E,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,15,19-pentaen-13-ynoate (1415668-79-9) → methyl (4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate (937738-63-1,937738-64-2)

Guidance literature:

With copper diacetate; silver nitrate; zinc; In methanol; diethyl ether; water; acetone; at 20 ℃; for 5h;

DOI:10.1039/C8OB03128B

Reference yield:

(S)-3-[(tert-butyldiphenylsilyl)oxy]-1-[(2S,3S)-3-[2-((4-methoxybenzyl)oxy)ethyl]oxiran-2-yl]propan-1-ol → methyl (4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate (937738-63-1,937738-64-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / aq. phosphate buffer; dichloromethane / 2 h / 20 °C / pH 6.8

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

3.2: 0.17 h / -78 - 20 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C

5.1: n-butyllithium; diisopropylamine / diethyl ether; hexane; tetrahydrofuran / 0.25 h / -78 °C

5.2: 0.25 h / -78 - 20 °C

6.1: zirconocene dichloride; diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 - 20 °C

6.2: 0.33 h / -78 - 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

8.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C

9.1: pyridinium p-toluenesulfonate; methanol / dichloromethane / 3 h / 20 °C

10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

10.2: 0.08 h / -78 - 20 °C

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C

11.2: 0.08 h / -78 - 0 °C

12.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; tert-butylamine / 0.25 h / 20 °C

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

14.1: zinc; copper diacetate; silver nitrate / diethyl ether; water; methanol; acetone / 5 h / 20 °C

With 2,6-dimethylpyridine; methanol; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; zirconocene dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; copper diacetate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; silver nitrate; dimethyl sulfoxide; tert-butylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; methanol; aq. phosphate buffer; diethyl ether; hexane; dichloromethane; water; acetone; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 10.1: |Swern Oxidation / 10.2: |Swern Oxidation / 12.1: |Sonogashira Cross-Coupling;

DOI:10.1039/C8OB03128B

Reference yield:

2-[(2S,3R)-3-((S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl)oxiran-2-yl]ethan-1-ol → methyl (4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoate (937738-63-1,937738-64-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

1.2: 0.17 h / -78 - 20 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C

3.1: n-butyllithium; diisopropylamine / diethyl ether; hexane; tetrahydrofuran / 0.25 h / -78 °C

3.2: 0.25 h / -78 - 20 °C

4.1: zirconocene dichloride; diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 - 20 °C

4.2: 0.33 h / -78 - 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C

7.1: pyridinium p-toluenesulfonate; methanol / dichloromethane / 3 h / 20 °C

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C

8.2: 0.08 h / -78 - 20 °C

9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C

9.2: 0.08 h / -78 - 0 °C

10.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; tert-butylamine / 0.25 h / 20 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

12.1: zinc; copper diacetate; silver nitrate / diethyl ether; water; methanol; acetone / 5 h / 20 °C

With 2,6-dimethylpyridine; methanol; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; zirconocene dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; copper diacetate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; silver nitrate; dimethyl sulfoxide; tert-butylamine; diisopropylamine; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 8.1: |Swern Oxidation / 8.2: |Swern Oxidation / 10.1: |Sonogashira Cross-Coupling;

DOI:10.1039/C8OB03128B

upstream raw materials:

[(4R,5S)-2,2-Dimethyl-5-((Z)-pent-2-enyl)-[1,3]dioxolan-4-yl]-methanol

C₁₁H₁₉IO₂

(3S,1E,5Z)-1-iodoocta-1,5-diene-3-ol

C₁₃H₂₂O₅

Downstream raw materials:

17(R)-Resolvin D₁

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