(4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate

Base Information

Chemical Name:(4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate
CAS No.:910215-36-0
Molecular Formula:C₂₆H₃₆O₅
Molecular Weight:428.569
Hs Code.:

Synonyms:(4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate

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Chemical Property of (4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate

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Technology Process of (4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate

There total 10 articles about (4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate 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: 64.0%

: 910215-26-8
(4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dien-1-ol

: 38867-17-3
(2E)-hepta-2,6-dienoic acid

: 910215-36-0
(4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate

Guidance literature:: With pyridine; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In toluene; at 20 ℃; for 24h;
DOI:10.1016/j.tetlet.2006.06.082

Reference yield:

: 910215-30-4
(4R,5R)-2-(4-methoxyphenyl)-5-methyl-4-vinyl-1,3-dioxane

: 910215-36-0
(4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 - 0 °C

2: 88 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: 82 percent / OsO₄; NaIO₄; 2,6-lutidine / dioxane; H₂O / 3 h / 20 °C

4: 72 percent / MgBr₂*OEt₂ / CH₂Cl₂ / 2 h / 20 °C

5: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 6 h / Heating

6: 94 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

7: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

8: 60 percent / DBU; NaI / tetrahydrofuran / 3 h / -78 - 0 °C

9: 96 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

10: 64 percent / 2,4,6-trichlorobenzoyl chloride; i-Pr₂NEt; pyridine / toluene / 24 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 2,6-di-tert-butyl-4-methylpyridine; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; sodium iodide; magnesium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 10: Yamaguchi esterification;
DOI:10.1016/j.tetlet.2006.06.082

Reference yield:

: 910215-31-5
(2R,3R)-3-(4-methoxybenzyloxy)-2-methylpent-4-en-1-ol

: 910215-36-0
(4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7-dienyl hepta-2,6-dienoate

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: 82 percent / OsO₄; NaIO₄; 2,6-lutidine / dioxane; H₂O / 3 h / 20 °C

3: 72 percent / MgBr₂*OEt₂ / CH₂Cl₂ / 2 h / 20 °C

4: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 6 h / Heating

5: 94 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

6: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

7: 60 percent / DBU; NaI / tetrahydrofuran / 3 h / -78 - 0 °C

8: 96 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

9: 64 percent / 2,4,6-trichlorobenzoyl chloride; i-Pr₂NEt; pyridine / toluene / 24 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 2,6-di-tert-butyl-4-methylpyridine; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; sodium iodide; magnesium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 9: Yamaguchi esterification;
DOI:10.1016/j.tetlet.2006.06.082