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

Base Information

Chemical Name:methyl 2-[(3R,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate
CAS No.:1267597-27-2
Molecular Formula:C₂₄H₃₈O₇
Molecular Weight:438.562
Hs Code.:

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

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

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

There total 18 articles about methyl 2-[(3R,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate 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: 92.0%

: 1267597-26-1
methyl 2-[(3R,6R,10S,E)-10-(tert-butyldimethylsilyloxy)-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate

: 1267597-27-2
methyl 2-[(3R,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1002/chem.201001752

Reference yield:

: 1251854-69-9
(S)-tert-butyldimethyl((5-(trimethylsilyl)pent-4-yn-2-yl)oxy)silane

: 1267597-27-2
methyl 2-[(3R,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: zinc trifluoromethanesulfonate; triethylamine; N-methyl ephedrine / toluene / 1 h / 20 °C / Inert atmosphere

2.2: 4 h / 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 / 72 h / 20 °C

5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 2 h / 20 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

7.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -80 °C / Inert atmosphere

7.2: 1.5 h / -80 - 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -80 °C / Inert atmosphere

8.2: 2 h / -80 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; N-methyl ephedrine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 5.1: Mitsunobu reaction / 7.1: Julia-Kocienski coupling / 7.2: Julia-Kocienski coupling;
DOI:10.1002/chem.201001752

Reference yield:

: 1267597-10-3
(4R)-5-(benzyloxy)-4-methylpentanal

: 1267597-27-2
methyl 2-[(3R,6R,10S,E)-10-hydroxy-6-(methoxymethoxy)-3-methylundec-1-enyl]-4,6-dimethoxybenzoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: zinc trifluoromethanesulfonate; triethylamine; N-methyl ephedrine / toluene / 1 h / 20 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

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

3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 72 h / 20 °C

4.1: triphenylphosphine; diethylazodicarboxylate / toluene / 2 h / 20 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

6.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -80 °C / Inert atmosphere

6.2: 1.5 h / -80 - 20 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -80 °C / Inert atmosphere

7.2: 2 h / -80 - 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With n-butyllithium; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; N-methyl ephedrine; In tetrahydrofuran; hexane; dichloromethane; toluene; 4.1: Mitsunobu reaction / 6.1: Julia-Kocienski coupling / 6.2: Julia-Kocienski coupling;
DOI:10.1002/chem.201001752