trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester

Base Information

• Chemical Name: trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester
• CAS No.: 908864-71-1
• Molecular Formula: C₂₀H₂₄F₃IO₅SSi
• Molecular Weight: 588.459
• Mol file: 908864-71-1.mol

Synonyms:trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester

Chemical Property of trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester

There total 8 articles about trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester 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: 96.3%

trifluoro-methanesulfonic acid 5-benzyloxy-3-hydroxy-2-iodo-phenyl ester (908864-77-7) + tert-butyldimethylsilyl chloride (18162-48-6) → trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester (908864-71-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 0.25h;

DOI:10.1021/ja064063e

Reference yield:

5-benzyloxy-2-iodo-benzene-1,3-diol (908864-75-5) → trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester (908864-71-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 82.2 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.25 h / -78 °C

2: 86.4 percent / cesium carbonate / 1,2-dimethoxy-ethane / 5 h / 90 °C

3: 96.3 percent / imidazole / dimethylformamide / 0.25 h / 25 °C

With 1H-imidazole; caesium carbonate; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja064063e

Reference yield:

1,3-di-O-acetyl-5-O-benzyl-benzophenone (850399-67-6) → trifluoro-methanesulfonic acid 5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-iodo-phenyl ester (908864-71-1)

Guidance literature:

Multi-step reaction with 5 steps

1: aq.NaOH / dioxane

2: 78.3 percent / KI; sodium hydrogencarbonate; iodine / tetrahydrofuran; H₂O / 1 h / 0 °C

3: 82.2 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.25 h / -78 °C

4: 86.4 percent / cesium carbonate / 1,2-dimethoxy-ethane / 5 h / 90 °C

5: 96.3 percent / imidazole / dimethylformamide / 0.25 h / 25 °C

With 1H-imidazole; sodium hydroxide; iodine; sodium hydrogencarbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja064063e

upstream raw materials:

trifluoro-methanesulfonic acid 5-benzyloxy-3-hydroxy-2-iodo-phenyl ester

tert-butyldimethylsilyl chloride

5-benzyloxy-2-iodo-benzene-1,3-diol

1,3-di-O-acetyl-5-O-benzyl-benzophenone

Downstream raw materials:

toluene-4-sulfonic acid 4-benzyloxy-3,5-dibromo-8-(tert-butyl-dimethyl-silanyloxy)-7,7,8-trimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-2-yl ester

4-benzyloxy-3,5-dibromo-8-(tert-butyl-dimethyl-silanyloxy)-7,7,8-trimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-2-ol

4-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-7,7,8-trimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-2-ol

4-benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,7,8-trimethoxy-bicyclo[4.2.0]octa-1,3,5-triene