4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin

Base Information

• Chemical Name: 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin
• CAS No.: 148238-40-8
• Molecular Formula: C₃₁H₂₈O₁₁
• Molecular Weight: 576.557
• Mol file: 148238-40-8.mol

Synonyms:4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin

Chemical Property of 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin

There total 3 articles about 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-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: 59.4%

4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin (147270-25-5) → 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin (148238-40-8)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; water; In acetone; at 0 ℃; for 3h;

DOI:10.1021/jm00064a002

Reference yield:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) → 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin (148238-40-8)

Guidance literature:

Multi-step reaction with 3 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

3: 59.4 percent / CrO₃, conc. H₂SO₄, H₂O / acetone / 3 h / 0 °C

With chromium(VI) oxide; lead(IV) acetate; osmium(VIII) oxide; sulfuric acid; boron trifluoride diethyl etherate; water; 4-methylmorpholine N-oxide; In dichloromethane; acetone;

DOI:10.1021/jm00064a002

Reference yield:

4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin (147238-65-1) → 4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-(2-oxo-2-hydroxyethyl)-4-desoxypodophyllotoxin (148238-40-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 59.4 percent / CrO₃, conc. H₂SO₄, H₂O / acetone / 3 h / 0 °C

With chromium(VI) oxide; lead(IV) acetate; osmium(VIII) oxide; sulfuric acid; water; 4-methylmorpholine N-oxide; In acetone;

DOI:10.1021/jm00064a002

upstream raw materials:

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

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

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

Downstream raw materials:

Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-(2-[1,4']bipiperidinyl-1'-yl-2-oxo-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

Carbonic acid benzyl ester 2,6-dimethoxy-4-{(5R,5aR,8aR,9S)-9-[(2-morpholin-4-yl-ethylcarbamoyl)-methyl]-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)-6-oxo-9-[(2-piperidin-1-yl-ethylcarbamoyl)-methyl]-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-(1-methyl-1H-pyrrol-2-yl)-ethylcarbamoyl]-methyl}-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