1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone

Base Information

• Chemical Name: 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone
• CAS No.: 1426679-88-0
• Molecular Formula: C₂₆H₃₆O₄Si
• Molecular Weight: 440.655

Synonyms:1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone

Chemical Property of 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone

There total 6 articles about 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone 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:

(R) 1-(4-methoxyphenyl)-5-hexen-1-ol (1172594-99-8) + 1-(4-(tert-butyldimethylsilyloxy)phenyl)prop-2-en-1-one (905266-48-0) → 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2R,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone (1426679-89-1) + 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone (1426679-88-0)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetasy.2013.01.005

Reference yield:

ethyl 5-(4-methoxyphenyl)-5-oxopentanoate (25305-58-2) → 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2R,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone (1426679-89-1) + 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone (1426679-88-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: formic acid; triethylamine; Noyori's catalyst / dichloromethane / 24 h / 40 °C / Inert atmosphere

2.1: 1H-imidazole; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

4.1: potassium tert-butylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4.2: 12 h / -78 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Inert atmosphere; Reflux

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; Noyori's catalyst; formic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 4.2: |Wittig Olefination;

DOI:10.1016/j.tetasy.2013.01.005

Reference yield:

(R)-ethyl 5-hydroxy-5-(4-methoxyphenyl)pentanoate (1426679-84-6) → 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2R,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone (1426679-89-1) + 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone (1426679-88-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3.2: 12 h / -78 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Inert atmosphere; Reflux

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; 3.2: |Wittig Olefination;

DOI:10.1016/j.tetasy.2013.01.005

upstream raw materials:

ethyl 5-(4-methoxyphenyl)-5-oxopentanoate

(R)-ethyl 5-hydroxy-5-(4-methoxyphenyl)pentanoate

(R)-ethyl 5-(tert-butyldimethylsilyloxy)-5-(4-methoxyphenyl)pentanoate

(R)-tert-butyl(1-(4-methoxyphenyl)hex-5-enyloxy)dimethylsilane

Downstream raw materials:

1-(4-hydroxyphenyl)-2-((2S,6R)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-yl)ethanone

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