2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester
• CAS No.: 128074-43-1
• Molecular Formula: C₂₈H₄₀O₈
• Molecular Weight: 504.621

Synonyms:2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester

Chemical Property of 2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester

There total 16 articles about 2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl 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: 85.0%

2-[(2E,8E,10E)-6-Benzyloxymethyl-12-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl]-malonic acid dimethyl ester (115349-76-3) → 2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester (128074-43-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield:

tert-Butyl-((2E,4E)-6-chloro-hexa-2,4-dienyloxy)-dimethyl-silane (115349-63-8) → 2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester (128074-43-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) THF, 1h, 0 degC to room temperature; 2.) THF/DMF, 12h, 0 degC to room temperature

2: 61 percent / LiCl / dimethylformamide; H₂O / 2.5 h / 165 °C

3: 82 percent / Dibal-H / CH₂Cl₂ / 0.5 h / -78 °C

4: 92 percent / NaH / tetrahydrofuran; dimethylformamide / 17 h / Ambient temperature

5: PPTS / H₂O; acetone / 5 h / 65 °C

6: imidazole / tetrahydrofuran / Ambient temperature

7: 1.) n-BuLi; 2.) Dibal-H / 1.) toluene, 0 degC then 150 h at room temperature; 2.) CH₂Cl₂, 15 min at -78 degC

8: LiCl, collidine, CH₃SO₂Cl / dimethylformamide / 15min, 0 degC then 1h at room temperature

9: NaH / tetrahydrofuran; dimethylformamide / 0 degC to room temperature then 12h at room temperature

With 1H-imidazole; 2,3,5-trimethyl-pyridine; n-butyllithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)96701-7

Reference yield:

(4E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-octa-4,6-dien-1-ol (115349-66-1) → 2-((2E,8E,10E)-6-Benzyloxymethyl-12-hydroxy-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester (128074-43-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / NaH / tetrahydrofuran; dimethylformamide / 17 h / Ambient temperature

2: PPTS / H₂O; acetone / 5 h / 65 °C

3: imidazole / tetrahydrofuran / Ambient temperature

4: 1.) n-BuLi; 2.) Dibal-H / 1.) toluene, 0 degC then 150 h at room temperature; 2.) CH₂Cl₂, 15 min at -78 degC

5: LiCl, collidine, CH₃SO₂Cl / dimethylformamide / 15min, 0 degC then 1h at room temperature

6: NaH / tetrahydrofuran; dimethylformamide / 0 degC to room temperature then 12h at room temperature

With 1H-imidazole; 2,3,5-trimethyl-pyridine; n-butyllithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)96701-7

upstream raw materials:

2-[(2E,8E,10E)-6-Benzyloxymethyl-12-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl]-malonic acid dimethyl ester

tert-Butyl-((2E,4E)-6-chloro-hexa-2,4-dienyloxy)-dimethyl-silane

(2E,4E)-6-((tert-butyldimethylsilyl)oxy)hexa-2,4-dien-1-ol

ethyl (2E,4E)-6-[(tetrahydro-2H-pyran-2-yl)oxy]hexa-2,4-dienoate

Downstream raw materials:

2-((2E,8E,10E)-6-Benzyloxymethyl-12-chloro-2-methoxymethoxy-3-methyl-dodeca-2,8,10-trienyl)-malonic acid dimethyl ester

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