N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide

Base Information

• Chemical Name: N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide
• CAS No.: 1365699-32-6
• Molecular Formula: C₂₉H₂₆N₂O₁₀
• Molecular Weight: 562.533

Synonyms:N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide

Chemical Property of N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide

Chemical Property:

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Technology Process of N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide

There total 1 articles about N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide 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: 92.0%

4-nitro-benzoyl chloride (122-04-3) + 4β-amino-4-deoxypodophyllotoxin (155252-35-0) → N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide (1365699-32-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2012.01.039

Reference yield: 98.0%

N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide (1365699-32-6) → N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-aminobenzamide (1365699-34-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate;

DOI:10.1016/j.bmc.2012.01.039

Reference yield:

N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide (1365699-32-6) → 4β-[4'-(5-bromothiophene-2-sulfonamido)benzamide]podophyllotoxin (1365699-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate

2: triethylamine / dichloromethane / 3 h / 20 °C

With palladium 10% on activated carbon; hydrogen; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1016/j.bmc.2012.01.039

upstream raw materials:

4-nitro-benzoyl chloride

4β-amino-4-deoxypodophyllotoxin

Downstream raw materials:

N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-aminobenzamide

4β-[4'-(5-bromothiophene-2-sulfonamido)benzamide]podophyllotoxin

4β-[4'-(benzo[c][1,2,5]thiadiazole-4-sulfonamido)benzamide]podophyllotoxin

4β-[4'-(quinoline-8-sulfonamido)benzamide]podophyllotoxin

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