(2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal

Base Information

Chemical Name:(2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal
CAS No.:1330569-06-6
Molecular Formula:C₃₀H₄₆O₅
Molecular Weight:486.692
Hs Code.:

Synonyms:(2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal

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Chemical Property of (2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal

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Technology Process of (2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal

There total 13 articles about (2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal 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:

: 1170989-57-7
ethyl (2E,4S)-4-(tert-butyldimethylsilyloxy)methyl-2-ethyl-hex-2-enoate

: 1330569-06-6
(2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal

Guidance literature:: Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.67 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

2.2: 21 h / 0 - 20 °C

3.1: acetic acid / tetrahydrofuran; water / 21.5 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 20 °C / Inert atmosphere

5.1: toluene / 1 h / -78 °C / Inert atmosphere; Molecular sieve

5.2: 18 h / 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / Reflux

7.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 7 h / 20 °C

8.1: sodium periodate / water; acetone / 0.5 h / 20 °C

9.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -40 °C / Inert atmosphere

9.2: 1 h / -78 °C / Inert atmosphere

10.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 6 h / 50 °C / Inert atmosphere

11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 - 20 °C / aq. phosphate buffer

12.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / N,N-dimethyl-formamide / 20 h / 70 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; potassium phenolate; water; sodium hydride; diisobutylaluminium hydride; caesium carbonate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; 4.1: Swern oxidation / 4.2: Swern oxidation / 9.2: Wittig reaction / 10.1: Miyaura vinylboronation / 12.1: Suzuki-Miyaura coupling;
DOI:10.1016/j.tet.2011.04.006

Reference yield:

: 1170989-60-2
(2E,4S)-4-(tert-butyldimethylsilyloxymethyl)-2-ethylhex-2-en-1-ol

: 1330569-06-6
(2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

1.2: 21 h / 0 - 20 °C

2.1: acetic acid / tetrahydrofuran; water / 21.5 h / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

4.1: toluene / 1 h / -78 °C / Inert atmosphere; Molecular sieve

4.2: 18 h / 20 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / Reflux

6.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 7 h / 20 °C

7.1: sodium periodate / water; acetone / 0.5 h / 20 °C

8.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -40 °C / Inert atmosphere

8.2: 1 h / -78 °C / Inert atmosphere

9.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 6 h / 50 °C / Inert atmosphere

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 - 20 °C / aq. phosphate buffer

11.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / N,N-dimethyl-formamide / 20 h / 70 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; potassium phenolate; water; sodium hydride; caesium carbonate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; 3.1: Swern oxidation / 3.2: Swern oxidation / 8.2: Wittig reaction / 9.1: Miyaura vinylboronation / 11.1: Suzuki-Miyaura coupling;
DOI:10.1016/j.tet.2011.04.006

Reference yield:

: 1170989-65-7
(2S,3E)-2-ethyl-4-(4-methoxybenzyloxymethyl)hex-3-en-1-ol

: 1330569-06-6
(2E,4S,5S,6R,7E,9E)-2,4,8-triethyl-10-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-6-methyldodeca-2,7,9-trienal

Guidance literature:: Multi-step reaction with 9 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: toluene / 1 h / -78 °C / Inert atmosphere; Molecular sieve

2.2: 18 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / Reflux

4.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 7 h / 20 °C

5.1: sodium periodate / water; acetone / 0.5 h / 20 °C

6.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -40 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

7.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 6 h / 50 °C / Inert atmosphere

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 - 20 °C / aq. phosphate buffer

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / N,N-dimethyl-formamide / 20 h / 70 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; potassium phenolate; water; caesium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 1.2: Swern oxidation / 6.2: Wittig reaction / 7.1: Miyaura vinylboronation / 9.1: Suzuki-Miyaura coupling;
DOI:10.1016/j.tet.2011.04.006