2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene

Base Information

• Chemical Name: 2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene
• CAS No.: 276880-04-7
• Molecular Formula: C₂₅H₂₉BrO₃Si
• Molecular Weight: 485.493
• Mol file: 276880-04-7.mol

Synonyms:2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene

Chemical Property of 2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene

There total 1 articles about 2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene 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: 98.0%

(4-bromo-3,5-dimethoxyphenyl)methanol (61367-62-2) + tert-butylchlorodiphenylsilane (58479-61-1) → 2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene (276880-04-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/ja000429q

Reference yield: 92.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene (276880-04-7) → 2,6-dimethoxy-4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzaldehyde (276880-05-8)

Guidance literature:

2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene; With tert.-butyl lithium; In diethyl ether; at -78 ℃;

N,N-dimethyl-formamide; In diethyl ether; at -78 - 20 ℃;

DOI:10.1021/ja000429q

Reference yield:

2-bromo-1,3-dimethoxy-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzene (276880-04-7) → (S)-5-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2-(1-butyl-5-chloropent-3-enyl)-1,3-dimethoxybenzene (276880-16-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: t-BuLi / ethanol; pentane / 0.5 h / -78 °C

1.2: 92 percent / ethanol; pentane / -78 - 20 °C

2.1: 70 percent / DBU; lithium chloride / acetonitrile / 36 h

3.1: 97 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0 °C

4.1: Amano P-30 lipase; 4A molecular sieves / hexane / 12 h / 20 °C

5.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: 80 percent / tetrahydrofuran / -78 - 20 °C

6.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: 99 percent / hydrogen / Pd/C / ethanol

8.1: 90 percent / DMSO; oxaloyl chloride; Et₃N / CH₂Cl₂ / -60 - 20 °C

9.1: 80 percent / DBU; LiCl / acetonitrile / 0 - 20 °C

10.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

11.1: 89 percent / N-chlorosuccinimide; dimethyl sulfide / CH₂Cl₂ / -30 - 0 °C

With sodium tetrahydroborate; N-chloro-succinimide; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; 4 A molecular sieve; Amano P-30 lipase; hydrogen; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile; pentane; 1.1: Metallation / 1.2: Formylation / 2.1: Masamune olefination / 3.1: Reduction / 4.1: enzymatic acetylation / 5.1: Metallation / 5.2: sigmatropic rearrangement / 6.1: Reduction / 7.1: Catalytic hydrogenation / 8.1: Oxidation / 9.1: Masamune olefination / 10.1: Reduction / 11.1: Chlorination;

DOI:10.1021/ja000429q

upstream raw materials:

(4-bromo-3,5-dimethoxyphenyl)methanol

tert-butylchlorodiphenylsilane

Downstream raw materials:

2,6-dimethoxy-4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzaldehyde

1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-one

rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol

(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-formyl-2,6-dimethoxyphenyl)undecanoate