4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

Base Information

Chemical Name:4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin
CAS No.:189454-56-6
Molecular Formula:C₃₉H₄₄N₂O₁₃
Molecular Weight:748.784
Hs Code.:

Synonyms:4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

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Chemical Property of 4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

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Technology Process of 4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

There total 12 articles about 4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin 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: 68.0%

: 68373-12-6
N-benzyloxycarbonyl-2-iodo-ethylamine

: 4-O-(3-azido-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

: 189454-56-6
4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide; for 120h; Ambient temperature;
DOI:10.1021/jm9800752

Reference yield:

: 23363-33-9
4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin

: 189454-56-6
4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

Guidance literature:: Multi-step reaction with 3 steps

1: 47 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

2: 88 percent / Et₃N, H₂ / 10 percent Pd/C / ethyl acetate / 2 h / Ambient temperature

3: 68 percent / Et₃N / dimethylformamide / 120 h / Ambient temperature

With boron trifluoride diethyl etherate; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm9800752

Reference yield:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 189454-56-6
4-O-(3-amino-N-ethylaminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-ribo-hexopyranosyl)-epipodophyllotoxin

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 47 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

3: 88 percent / Et₃N, H₂ / 10 percent Pd/C / ethyl acetate / 2 h / Ambient temperature

4: 68 percent / Et₃N / dimethylformamide / 120 h / Ambient temperature

With boron trifluoride diethyl etherate; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm9800752