4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin

Base Information

• Chemical Name: 4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin
• CAS No.: 1611490-29-9
• Molecular Formula: C₂₉H₃₂N₂O₈
• Molecular Weight: 536.582

Synonyms:4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin

Chemical Property of 4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin

Chemical Property:

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Technology Process of 4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin

There total 6 articles about 4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin 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:

C29H30N2O8 → 4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin (1611490-29-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 4h;

DOI:10.1016/j.ejmech.2014.08.006

Reference yield:

4-demethylpodophyllotoxin (40505-27-9) → 4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin (1611490-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid; sodium azide / dichloromethane / 4.25 h / 20 °C / Cooling with ice; Inert atmosphere

2: palladium 10% on activated carbon; ammonium formate / ethyl acetate / 8 h / 60 °C

3: acetic acid / methanol / 12 h / 20 °C

4: sodium tetrahydroborate / methanol / 4 h / 0 °C

With sodium tetrahydroborate; sodium azide; palladium 10% on activated carbon; ammonium formate; acetic acid; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/j.ejmech.2014.08.006

Reference yield:

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) → 4β-N-[5-{((dimethylamino)methyl)furan-2-yl}methyl]amido-4'-demethyl-4-desoxypodophyllotoxin (1611490-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid / 4 h / 40 °C

2: manganese(IV) oxide / dichloromethane / 2 h / 20 °C

3: acetic acid / methanol / 12 h / 20 °C

4: sodium tetrahydroborate / methanol / 4 h / 0 °C

With manganese(IV) oxide; sodium tetrahydroborate; acetic acid; In methanol; dichloromethane; 1: |Mannich Aminomethylation;

DOI:10.1016/j.ejmech.2014.08.006

upstream raw materials:

4-demethylpodophyllotoxin

5-<(dimethylamino)methyl>furfural

(5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

(2-furyl)methyl alcohol

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