C₂₂H₂₀N₂O₃

Base Information

• Chemical Name: C₂₂H₂₀N₂O₃
• CAS No.: 205051-54-3
• Molecular Formula: C₂₂H₂₀N₂O₃
• Molecular Weight: 360.412
• Mol file: 205051-54-3.mol

Synonyms:C₂₂H₂₀N₂O₃

Chemical Property of C₂₂H₂₀N₂O₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₂H₂₀N₂O₃

There total 11 articles about C₂₂H₂₀N₂O₃ 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:

8-O-tert-butyldimethylsilylduocarmycin B2 (129953-15-7) → C22H20N2O3 (205051-54-3)

Guidance literature:

Multi-step reaction with 8 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: nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

7: NaOMe / methanol / 1 h / Ambient temperature

8: dimethylformamide / 0.83 h

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromobenzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; dimedone; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm990094r

Reference yield:

8-O-(tert-butyldimethylsilyl)-2-methyl-3-(benzyloxycarbonyl)-A-ring-pyrrole-duocarmycin B2 (246034-77-5) → C22H20N2O3 (205051-54-3)

Guidance literature:

Multi-step reaction with 5 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: nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

4: NaOMe / methanol / 1 h / Ambient temperature

5: dimethylformamide / 0.83 h

With bromobenzene; tetrabutyl ammonium fluoride; ammonium formate; sodium methylate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm990094r

Reference yield:

8-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-methyl-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2-carboxylic acid benzyl ester → C22H20N2O3 (205051-54-3)

Guidance literature:

Multi-step reaction with 6 steps

1: BF₃*Et₂O / CHCl₃ / 17.5 h / Ambient temperature

2: 80 percent / 25 percent aq. HCO₂NH₄ / 10 percent Pd/C / tetrahydrofuran / 0.5 h / Ambient temperature

3: 60 percent / PhBr / 10 h / 165 °C

4: nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

5: NaOMe / methanol / 1 h / Ambient temperature

6: dimethylformamide / 0.83 h

With bromobenzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonium formate; sodium methylate; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm990094r

upstream raw materials:

p-nitrophenyl ester of 4-methoxycinnamic acid

C₁₂H₁₂N₂O

2-methyl-A-ring pyrrole-duocarmycin A

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

Downstream raw materials:

4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂

C₂₅H₂₇N₃O₃