(4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester

Base Information

• Chemical Name: (4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester
• CAS No.: 201004-78-6
• Molecular Formula: C₃₇H₅₆O₅
• Molecular Weight: 580.849

Synonyms:

Chemical Property of (4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester

There total 7 articles about (4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl 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:

(4E,8E,12E,16Z)-18-[3,4-Dimethyl-5-(tetrahydro-pyran-2-yloxy)-2-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester (201004-77-5) → (4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester (201004-78-6)

Guidance literature:

With cesium fluoride; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 120 ℃; for 2h; Yield given;

DOI:10.1002/(SICI)1099-0690(199801)1998:1<43::AID-EJOC43>3.0.CO;2-L

Reference yield:

(4E,8E,12E)-14-Acetoxy-4,8,12-trimethyl-tetradeca-4,8,12-trienoic acid methyl ester (176246-20-1) → (4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester (201004-78-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / Pd(dba)2, LiCl / dimethylformamide

2: 95 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

3: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / Ambient temperature

4: 70 percent / 1.) s-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 30 min; 2.) room temp., 2 h

5: 83 percent / propionic acid / 1 h / 140 °C

6: cesium fluoride / hexamethylphosphoric acid triamide / 2 h / 120 °C

With pyridine; lithium aluminium tetrahydride; sec.-butyllithium; Dess-Martin periodane; propionic acid; cesium fluoride; lithium chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1099-0690(199801)1998:1<43::AID-EJOC43>3.0.CO;2-L

Reference yield:

{2-[2,3-Dimethyl-4-(tetrahydro-pyran-2-yloxy)-6-trimethylstannanyl-phenoxymethoxy]-ethyl}-trimethyl-silane → (4E,8E,12E,16Z)-18-[2-Hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester (201004-78-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / Pd(dba)2, LiCl / dimethylformamide

2: 95 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

3: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / Ambient temperature

4: 70 percent / 1.) s-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 30 min; 2.) room temp., 2 h

5: 83 percent / propionic acid / 1 h / 140 °C

6: cesium fluoride / hexamethylphosphoric acid triamide / 2 h / 120 °C

With pyridine; lithium aluminium tetrahydride; sec.-butyllithium; Dess-Martin periodane; propionic acid; cesium fluoride; lithium chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1099-0690(199801)1998:1<43::AID-EJOC43>3.0.CO;2-L

upstream raw materials:

(4E,8E,12E,16Z)-18-[3,4-Dimethyl-5-(tetrahydro-pyran-2-yloxy)-2-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester

(4E,8E,12E)-14-Acetoxy-4,8,12-trimethyl-tetradeca-4,8,12-trienoic acid methyl ester

(4E,8E,12E)-14-[3,4-Dimethyl-5-(tetrahydro-pyran-2-yloxy)-2-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-4,8,12-trimethyl-tetradeca-4,8,12-trienoic acid methyl ester

(6E,10E,14Z)-16-[3,4-Dimethyl-5-(tetrahydro-pyran-2-yloxy)-2-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-2,6,10,14-tetramethyl-hexadeca-1,6,10,14-tetraen-3-ol

Downstream raw materials:

(4E,8E,12E,16Z)-18-[2-Acetoxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester

(4E,8E,12E,16Z)-18-(2-Acetoxy-5-hydroxy-3,4-dimethyl-phenyl)-4,8,12,16-tetramethyl-octadeca-4,8,12,16-tetraenoic acid ethyl ester

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