11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate

Base Information

• Chemical Name: 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate
• CAS No.: 845863-38-9
• Molecular Formula: C₃₆H₄₀N₂O₁₁
• Molecular Weight: 676.72
• Mol file: 845863-38-9.mol

Synonyms:11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate

Chemical Property of 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate

There total 6 articles about 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate 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: 65.0%

N,N,N'-trimethylpropane-1,3-diamine (4543-96-8) + 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-(p-nitrophenyl)carbonate (845863-33-4) → 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate (845863-38-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jm0495733

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate (845863-38-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / Et₃N / CH₂Cl₂

2: 97 percent / pyridine / CH₂Cl₂ / 20 °C

3: 65 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With pyridine; triethylamine; In dichloromethane;

DOI:10.1021/jm0495733

Reference yield:

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol (153230-77-4) → 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate (845863-38-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves / CH₂Cl₂ / 2 h

1.2: tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h

2.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 23 h

3.1: 82 percent / Et₃N / CH₂Cl₂

4.1: 97 percent / pyridine / CH₂Cl₂ / 20 °C

5.1: 65 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With pyridine; molecular sieve; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0495733

upstream raw materials:

N,N,N'-trimethylpropane-1,3-diamine

11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-(p-nitrophenyl)carbonate

benzyl chloroformate

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol

Refernces