4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

Base Information

• Chemical Name: 4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin
• CAS No.: 851167-15-2
• Molecular Formula: C₃₆H₄₂FNO₉Si
• Molecular Weight: 679.815

Synonyms:4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

Chemical Property of 4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

Chemical Property:

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Technology Process of 4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

There total 2 articles about 4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-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: 92.0%

4-β-isocyanate-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (851166-94-4) + 2-(4-Fluorophenyl)ethanol (7589-27-7) → 4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (851167-15-2)

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1039/b416862c

Reference yield:

4-β-amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (692755-45-6) → 4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (851167-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 92 percent / CH₂Cl₂ / 20 °C

With triethylamine; In dichloromethane;

DOI:10.1039/b416862c

Reference yield: 75.0%

4-β-(4-fluorophenylethyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (851167-15-2) → [(5S,5aS,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]-carbamic acid 2-(4-fluoro-phenyl)-ethyl ester

Guidance literature:

With Dowex 50 20-200 ion-exchange resin; In methanol; at 20 ℃; for 16h;

DOI:10.1039/b416862c

upstream raw materials:

4-β-isocyanate-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

2-(4-Fluorophenyl)ethanol

4-β-amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

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