8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B₂

Base Information

• Chemical Name: 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B₂
• CAS No.: 205050-86-8
• Molecular Formula: C₃₇H₄₂BrN₃O₆Si
• Molecular Weight: 732.746
• Mol file: 205050-86-8.mol

Synonyms:8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B₂

Chemical Property of 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B₂

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B₂

There total 9 articles about 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B₂ 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: 51.0%

benzoic acid anhydride (93-97-0) + 8-O-(tert-butyldimethylsilyl)-2-methyl-A-ring-pyrrole-duocarmyicin B2 (183240-29-1) → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B2 (205050-86-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 14.6h; Ambient temperature;

DOI:10.1021/jm990094r

Reference yield:

8-O-tert-butyldimethylsilylduocarmycin B2 (129953-15-7) → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B2 (205050-86-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 5.70 g / K₂CO₃ / 5.67 h / 0 °C

2: 35 percent / NaBH₄ / various solvent(s) / 105 h / 0 °C

3: 71 percent / BF₃*Et₂O / CHCl₃ / 17.5 h / Ambient temperature

4: 99 percent / Pd(PPh₃)4, dimedone / tetrahydrofuran / 1 h / Ambient temperature

5: 60 percent / PhBr / 10 h / 165 °C

6: 51 percent / BF₃*Et₂O / CH₂Cl₂ / 14.6 h / Ambient temperature

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromobenzene; boron trifluoride diethyl etherate; potassium carbonate; dimedone; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1021/jm990094r

Reference yield:

8-O-(tert-butyldimethylsilyl)-2-methyl-3-(benzyloxycarbonyl)-A-ring-pyrrole-duocarmycin B2 (246034-77-5) → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B2 (205050-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 25 percent aq. HCO₂NH₄ / 10 percent Pd/C / tetrahydrofuran / 0.5 h / Ambient temperature

2: 60 percent / PhBr / 10 h / 165 °C

3: 51 percent / BF₃*Et₂O / CH₂Cl₂ / 14.6 h / Ambient temperature

With bromobenzene; boron trifluoride diethyl etherate; ammonium formate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm990094r

upstream raw materials:

benzoic acid anhydride

8-O-(tert-butyldimethylsilyl)-2-methyl-A-ring-pyrrole-duocarmyicin B₂

8-O-tert-butyldimethylsilylduocarmycin B₂

8-O-(tert-butyldimethylsilyl)-2-methyl-3-carboxy-A-ring-pyrrole-duocarmicyn B₂