10(S),17(S)-DiHDoHE

Base Information

• Chemical Name: 10(S),17(S)-DiHDoHE
• CAS No.: 871826-47-0
• Molecular Formula: C22H32O4
• Molecular Weight: 360.48700
• Mol file: 871826-47-0.mol

Synonyms:

Chemical Property of 10(S),17(S)-DiHDoHE

Chemical Property:

• PSA: 77.76000
• LogP: 4.49050

Purity/Quality:

99% ^*data from raw suppliers

10(S),17(S)-DiHDHA ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 10(S),17(S)-DiHDoHE

There total 19 articles about 10(S),17(S)-DiHDoHE 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: 77.0%

methyl (10S,17S,4Z,7Z,11E,13Z,15E,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexenoate → (4Z,7Z,10S,11E,13Z,15E,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoic acid (871826-47-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 5 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.8b01973

Reference yield:

C27H40O5 → (4Z,7Z,10S,11E,13Z,15E,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoic acid (871826-47-0)

Guidance literature:

C₂₇H₄₀O₅; With pyridinium p-toluenesulfonate; In methanol; at 4 ℃; for 0.25h;

With lithium hydroxide; In tetrahydrofuran; water; for 5h;

Reference yield:

(3S,6Z)-1-[bis(4-methoxyphenyl)(phenyl)methoxy]-7-chlorohept-6-en-4-yn-3-ol → (4Z,7Z,10S,11E,13Z,15E,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoic acid (871826-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper(l) iodide; piperidine / benzene / 0.17 h / Inert atmosphere

1.2: 3 h / 20 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h

2.2: 2 h / 4 °C

3.1: 4-methylmorpholine N-oxide / dichloromethane / 0.25 h / Molecular sieve

3.2: 1 h

4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

4.2: 2.17 h / 0 - 5 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: pyridinium p-toluenesulfonate / methanol / 0.25 h / 4 °C

7.2: 5 h

With piperidine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; benzene;

Refernces

• 1、 Sancéau, Jean-Yves,Maltais, René,Poirier, Donald,Marette, André. "Total Synthesis of the Antidiabetic (Type 2) Lipid Mediator Protectin DX/PDX". . p. 495 - 505. Retrieved 2019/01/24.