5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal

Base Information

• Chemical Name: 5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal
• CAS No.: 648433-61-8
• Molecular Formula: C₂₉H₄₄O₆Si
• Molecular Weight: 516.75

Synonyms:5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal

Chemical Property of 5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal

Chemical Property:

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Technology Process of 5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal

There total 10 articles about 5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal 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: 80.0%

5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentan-1-ol (648433-60-7) → 5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal (648433-61-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 2h;

DOI:10.1021/ja039124c

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal (648433-61-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.25 g / imidazole / dimethylformamide / 3 h

2: potassium carbonate / methanol / 3 h / 20 °C

3: 1.52 g / quinoline; H₂ / Pd/BaSO₄ / toluene / 12 h / 20 °C / 760 Torr

4: 38 percent / aq. OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 4 h / 20 °C

5: pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 20 °C

6: 78 mg / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

7: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With 1H-imidazole; quinoline; osmium(VIII) oxide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; Pd-BaSO₄; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ja039124c

Reference yield:

(2R,3S)-3-(2,3-Dimethoxy-4-methyl-phenyl)-2-methyl-5-trimethylsilanyl-pent-4-yn-1-ol (648433-65-2) → 5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentanal (648433-61-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.25 g / imidazole / dimethylformamide / 3 h

2: potassium carbonate / methanol / 3 h / 20 °C

3: 1.52 g / quinoline; H₂ / Pd/BaSO₄ / toluene / 12 h / 20 °C / 760 Torr

4: 38 percent / aq. OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 4 h / 20 °C

5: pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 20 °C

6: 78 mg / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

7: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With 1H-imidazole; quinoline; osmium(VIII) oxide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; Pd-BaSO₄; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ja039124c

upstream raw materials:

5-(tert-butyldimethylsilanyloxy)-3-(2,3-dimethoxy-4-methylphenyl)-2-(4-methoxybenzyloxy)-4-methylpentan-1-ol

p-Anisaldehyde dimethyl acetal

tert-butyldimethylsilyl chloride

(2R,3S)-3-(2,3-Dimethoxy-4-methyl-phenyl)-2-methyl-5-trimethylsilanyl-pent-4-yn-1-ol

Downstream raw materials:

4-(2,3-dimethoxy-4-methylphenyl)-3-(4-methoxybenzyloxy)-5-methyl-tetrahydropyran-2-one

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