(5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one

Base Information

• Chemical Name: (5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one
• CAS No.: 1447716-64-4
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37

Synonyms:(5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one

Chemical Property of (5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one

There total 3 articles about (5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one 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:

(4R,5R,Z)-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienoic acid (1447716-57-5) → (5R,6S,7S)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one (1447716-58-6) + (5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one (1447716-64-4)

Guidance literature:

With (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride; [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; p-benzoquinone; In 1,4-dioxane; at 45 ℃; for 72h; Overall yield = 40 %; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.05.137

Reference yield:

(4R,5R)-4-allyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (1415934-55-2) → (5R,6S,7S)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one (1447716-58-6) + (5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one (1447716-64-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 - 20 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane; water / 2 h / Cooling with ice; Inert atmosphere

3.1: sodium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

3.2: -78 - 0 °C / Inert atmosphere

4.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 50 °C / Inert atmosphere

5.1: [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; p-benzoquinone; (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride / 1,4-dioxane / 72 h / 45 °C / Inert atmosphere

With (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride; lithium hydroxide monohydrate; [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-benzoquinone; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water;

DOI:10.1016/j.tetlet.2013.05.137

Reference yield:

(2R,3R)-3-(4-methoxybenzyloxy)-2-methylhex-5-en-1-ol (1415934-56-3) → (5R,6S,7S)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one (1447716-58-6) + (5R,6S,7R)-6-(4-methoxybenzyloxy)-3,5-dimethyl-7-vinyl-6,7-dihydrooxepin-2(5H)-one (1447716-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Dess-Martin periodane / dichloromethane; water / 2 h / Cooling with ice; Inert atmosphere

2.1: sodium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 50 °C / Inert atmosphere

4.1: [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; p-benzoquinone; (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride / 1,4-dioxane / 72 h / 45 °C / Inert atmosphere

With (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride; lithium hydroxide monohydrate; [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-benzoquinone; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1016/j.tetlet.2013.05.137

upstream raw materials:

(4R,5R)-4-allyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(2R,3R)-3-(4-methoxybenzyloxy)-2-methylhex-5-en-1-ol

(4R,5R,Z)-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienoic acid

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