Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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

Base Information

• Chemical Name: Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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
• CAS No.: 642409-91-4
• Molecular Formula: C₃₇H₃₈O₁₅
• Molecular Weight: 722.7

Synonyms:Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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

Chemical Property of Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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

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Technology Process of Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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

There total 8 articles about Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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 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: 80.0%

chloro-acetic acid 6-[9-(4-benzyloxycarbonyloxy-3,5-dimethoxy-phenyl)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-8-chloroacetoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (642409-89-0) → Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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 (642409-91-4)

Guidance literature:

With methanol; zinc diacetate; for 1.15h; Heating;

DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

4'-demethylepipodophyllotoxin (6559-91-7) → Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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 (642409-91-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 - 20 °C

3: 27 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 0.67 h / 20 °C

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 20 °C

5: 82 percent / aq. NaClO₂; NH₂SO₃H / 2-methyl-propan-2-ol / 1 h / 20 °C

6: 97 percent / LiEt₃BH / tetrahydrofuran / 1 h / 0 °C

7: 83 percent / DCC; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

8: 80 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

9: 85 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

10: 40 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -60 - -10 °C

11: 80 percent / Zn(OAc)2; MeOH / 1.15 h / Heating

With 2,6-dimethylpyridine; methanol; dmap; sodium chlorite; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; aminosulfonic acid; zinc diacetate; tetrabutyl ammonium fluoride; lithium triethylborohydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 4: Dess-Martin oxidation / 10: Kuhn-like coupling;

DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-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 (642409-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 40 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -60 - -10 °C

3: 80 percent / Zn(OAc)2; MeOH / 1.15 h / Heating

With methanol; boron trifluoride diethyl etherate; zinc diacetate; triethylamine; In dichloromethane; 2: Kuhn-like coupling;

DOI:10.1016/j.bmcl.2003.08.044

upstream raw materials:

chloro-acetic acid 6-[9-(4-benzyloxycarbonyloxy-3,5-dimethoxy-phenyl)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-8-chloroacetoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

4'-demethylepipodophyllotoxin

benzyl chloroformate

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol

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