(3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

Base Information

• Chemical Name: (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one
• CAS No.: 901774-51-4
• Molecular Formula: C₂₆H₂₄O₆
• Molecular Weight: 432.473

Synonyms:(3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

Chemical Property of (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

There total 2 articles about (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one 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:

keto rocaglate (901774-46-7) → (3R,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one (959461-41-7) + (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one (901774-51-4)

Guidance literature:

With water; lithium chloride; In dimethyl sulfoxide; at 100 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1021/ja062621j

Reference yield:

trimethoxy cyclopenta[bc]benzopyran → (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one (901774-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaOMe / methanol / 0.33 h / 60 °C

2: lithium chloride; water / dimethylsulfoxide / 12 h / 100 °C

With water; sodium methylate; lithium chloride; In methanol; dimethyl sulfoxide;

DOI:10.1021/ja062621j

Reference yield: 66.0%

(3R,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one (959461-41-7) + (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one (901774-51-4) → exo rocaglaol + endo rocaglaol

Guidance literature:

(3R,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one; (3S,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one; With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at 20 ℃; for 3h;

With ammonium chloride; In water; acetonitrile;

With sodium L-tartrate; potassium L-tartrate; In water; acetonitrile; at 20 ℃; for 0.5h;

upstream raw materials:

keto rocaglate

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