4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate

Base Information

• Chemical Name: 4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate
• CAS No.: 845863-25-4
• Molecular Formula: C₃₅H₃₈N₂O₁₁
• Molecular Weight: 662.694

Synonyms:4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate

Chemical Property of 4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate

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Technology Process of 4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate

There total 2 articles about 4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]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: 85.0%

1-amino-3-(dimethylamino)propane (109-55-7) + 4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-(p-nitrophenyl)carbonate (845863-22-1) → 4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate (845863-25-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jm0495733

Reference yield:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) → 4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate (845863-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / CH₂Cl₂ / 0.75 h / 20 °C

2: 85 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; triethylamine; In dichloromethane;

DOI:10.1021/jm0495733

Reference yield: 76.0%

4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]]carbamate (845863-25-4) → (3-Dimethylamino-propyl)-carbamic acid (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h;

DOI:10.1021/jm0495733

upstream raw materials:

1-amino-3-(dimethylamino)propane

4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-(p-nitrophenyl)carbonate

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin

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