2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid

Base Information

• Chemical Name: 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid
• CAS No.: 1267597-42-1
• Molecular Formula: C₂₃H₃₆O₇
• Molecular Weight: 424.535
• Mol file: 1267597-42-1.mol

Synonyms:2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid

Chemical Property of 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid

There total 19 articles about 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic 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: 95.0%

methyl 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate (1267597-41-0) → 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid (1267597-42-1)

Guidance literature:

With water; potassium hydroxide; In ethanol; Reflux; Inert atmosphere;

DOI:10.1002/chem.201001752

Reference yield:

(S)-tert-butyldimethyl((5-(trimethylsilyl)pent-4-yn-2-yl)oxy)silane (1251854-69-9) → 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid (1267597-42-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / methanol / 2 h / 20 °C / Inert atmosphere

2.1: zinc trifluoromethanesulfonate; triethylamine; N-methyl ephedrine / toluene / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 20 °C

5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 20 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -80 °C / Inert atmosphere

7.2: -80 - 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere

8.2: -80 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

10.1: water; potassium hydroxide / ethanol / Reflux; Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hydroxide; diethylazodicarboxylate; N-methyl ephedrine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; 7.1: Julia-Kocienski coupling / 7.2: Julia-Kocienski coupling;

DOI:10.1002/chem.201001752

Reference yield:

(S)-5-(benzyloxy)-4-methylpentan-1-ol (887706-39-0) → 2-[(3S,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoic acid (1267597-42-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -90 °C / Inert atmosphere

1.2: -90 - 20 °C / Inert atmosphere

2.1: zinc trifluoromethanesulfonate; triethylamine; N-methyl ephedrine / toluene / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 20 °C

5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 20 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -80 °C / Inert atmosphere

7.2: -80 - 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere

8.2: -80 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

10.1: water; potassium hydroxide / ethanol / Reflux; Inert atmosphere

With n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hydroxide; diethylazodicarboxylate; N-methyl ephedrine; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation / 7.1: Julia-Kocienski coupling / 7.2: Julia-Kocienski coupling;

DOI:10.1002/chem.201001752

upstream raw materials:

(S)-5-(benzyloxy)-4-methylpentan-1-ol

(S)-tert-butyldimethyl((5-(trimethylsilyl)pent-4-yn-2-yl)oxy)silane

(2S,5S,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-2-methyldec-6-yn-5-ol

[(2S,6S,9S)-10-(benzyloxy)-6-(methoxymethoxy)-9-methyldec-4-yn-2-yloxy](tert-butyl)dimethylsilane