4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin

Base Information

• Chemical Name: 4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin
• CAS No.: 147270-25-5
• Molecular Formula: C₃₁H₂₈O₁₀
• Molecular Weight: 560.557
• Mol file: 147270-25-5.mol

Synonyms:4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin

Chemical Property of 4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin

There total 5 articles about 4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin 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:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) → 4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin (147270-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95.8 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

2: 1.) OsO₄, N-methylmorpholine N-oxide (NMO), 2.) Pb(OAc)4 / 1.) acetone, RT, 1 h, 2.) benzene, RT, 0.5 h

With lead(IV) acetate; osmium(VIII) oxide; boron trifluoride diethyl etherate; 4-methylmorpholine N-oxide; In dichloromethane;

DOI:10.1021/jm00064a002

Reference yield:

trimethylsiloxyethene (6213-94-1) + 4′-demethyl-4′-O-(benzyloxycarbonyl) (epi)-podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate → C31H28O10 + 4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin (147270-25-5)

Guidance literature:

trimethylsiloxyethene; 4′-demethyl-4′-O-(benzyloxycarbonyl) (epi)-podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); In dichloromethane; at 20 ℃; for 4h; Overall yield = 82 %; Overall yield = 23 mg; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.joc.7b00485

Reference yield:

4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin (147238-65-1) → 4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin (147270-25-5)

Guidance literature:

With lead(IV) acetate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; Yield given. Multistep reaction; 1.) acetone, RT, 1 h, 2.) benzene, RT, 0.5 h;

DOI:10.1021/jm00064a002

upstream raw materials:

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

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

trimethylsiloxyethene

4'-demethylepipodophyllotoxin

Downstream raw materials:

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

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

Carbonic acid benzyl ester 4-((5R,5aR,8aR,9S)-9-{2-[(2-hydroxy-1-hydroxymethyl-ethyl)-methyl-amino]-ethyl}-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'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin