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

Base Information

• Chemical Name: 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
• CAS No.: 157158-56-0
• Molecular Formula: C₃₈H₃₈N₂O₁₀
• Molecular Weight: 682.727
• Mol file: 157158-56-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of 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

There total 5 articles about 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 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) → 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 (157158-56-0)

Guidance literature:

Multi-step reaction with 5 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

4: (dimethylamino)pyridine (DMAP) / ethyl acetate / 0.5 h / 0 °C

5: ethyl acetate / 0.5 h

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

DOI:10.1021/jm00064a002

Reference yield:

4'-demethyl-4'-O-(benzyloxycarbonyl)-4β-allyl-4-desoxypodophyllotoxin (147238-65-1) → 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 (157158-56-0)

Guidance literature:

Multi-step reaction with 4 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

3: (dimethylamino)pyridine (DMAP) / ethyl acetate / 0.5 h / 0 °C

4: ethyl acetate / 0.5 h

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

DOI:10.1021/jm00064a002

Reference yield:

4′-demethyl-4′-O-(benzyloxycarbonyl) 4-deoxy-4-(2-formylethyl)-(epi)-podophyllotoxin (147270-25-5) → 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 (157158-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 59.4 percent / CrO₃, conc. H₂SO₄, H₂O / acetone / 3 h / 0 °C

2: (dimethylamino)pyridine (DMAP) / ethyl acetate / 0.5 h / 0 °C

3: ethyl acetate / 0.5 h

With chromium(VI) oxide; dmap; sulfuric acid; water; In ethyl acetate; acetone;

DOI:10.1021/jm00064a002

upstream raw materials:

2-(2-Aminoethyl)-1-methylpyrrole

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

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

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