4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin

Base Information

• Chemical Name: 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin
• CAS No.: 147238-65-1
• Molecular Formula: C₃₂H₃₀O₉
• Molecular Weight: 558.585
• Mol file: 147238-65-1.mol

Synonyms:4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin

Chemical Property of 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin

There total 5 articles about 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-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: 95.8%

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) + allyl-trimethyl-silane (762-72-1) → 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin (147238-65-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jm00064a002

Reference yield: 85.0%

Carbonic acid benzyl ester 4-((5R,5aR,8aR,9S)-9-ethanesulfinyl-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester + allyl-trimethyl-silane (762-72-1) → 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin (147238-65-1)

Guidance literature:

With trifluoromethanesulfonic acid anhydride; In dichloromethane; at -78 ℃;

DOI:10.1021/ol005732a

Reference yield:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) → 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin (147238-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

2: m-CPBA / CH₂Cl₂ / 0.08 h / -78 °C

3: 85 percent / trifluoromethanesulfonic anhydride / CH₂Cl₂ / -78 °C

With boron trifluoride diethyl etherate; trifluoromethanesulfonic acid anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1: Substitution / 2: Oxidation / 3: sulfoxide activation;

DOI:10.1021/ol005732a

upstream raw materials:

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

allyl-trimethyl-silane

Carbonic acid benzyl ester 4-((5R,5aR,8aR,9S)-9-ethylsulfanyl-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester

4'-demethylepipodophyllotoxin