5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde

Base Information

• Chemical Name: 5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde
• CAS No.: 808766-15-6
• Molecular Formula: C₁₅H₂₄O₄Si
• Molecular Weight: 296.439
• Mol file: 808766-15-6.mol

Synonyms:5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde

Chemical Property of 5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde

There total 1 articles about 5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde 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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,5-dihydroxy-4-methoxy-3-methyl-benzaldehyde (622852-28-2) → 5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde (808766-15-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/ja0447154

Reference yield: 95.0%

5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde (808766-15-6) → 4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-methoxy-2-methyl-phenol (808765-99-3)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/ja0447154

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methoxy-3-methyl-benzaldehyde (808766-15-6) → [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane (808766-02-1)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 78 percent / acetonitrile / 2 h / 20 °C

3: DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

4: 21 mg / Et₃N / toluene / 0.5 h / Heating

With dmap; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; In hexane; dichloromethane; toluene; acetonitrile; 4: Wittig olefination;

DOI:10.1021/ja0447154

upstream raw materials:

tert-butyldimethylsilyl chloride

2,5-dihydroxy-4-methoxy-3-methyl-benzaldehyde

Downstream raw materials:

4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-methoxy-2-methyl-phenol

(5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-1,19:5,9-diepoxybenzo[18]annulen-3(5H)-one

[2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane