3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal

Base Information

• Chemical Name: 3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal
• CAS No.: 1417802-03-9
• Molecular Formula: C₃₁H₂₈O₇
• Molecular Weight: 512.559

Synonyms:3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal

Chemical Property of 3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal

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Technology Process of 3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal

There total 19 articles about 3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal 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%

4-((6-(2-(3-hydroxypropyl)-4-methoxyphenyl)-3,7-dimethoxy-9,10-dihydrophenanthren-4-yl)oxy)-2H-pyran-2-one (1417802-02-8) → 3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal (1417802-03-9)

Guidance literature:

With dichloromethane; potassium carbonate; Dess-Martin periodane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol303390a

Reference yield:

5'-(benzyloxy)-2-isopropoxy-3,4'-dimethoxy-2',6-divinyl-1,1'-biphenyl (1417801-87-6) → 3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal (1417802-03-9)

Guidance literature:

Multi-step reaction with 7 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 22 h / 50 °C / Inert atmosphere

2: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 24 h / 31029.7 Torr / Inert atmosphere

3: pyridine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

4: water; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium bromide / 1,4-dioxane / 36 h / 80 °C / Inert atmosphere

5: boron trichloride; dichloromethane / dichloromethane / 0.5 h / -78 - -30 °C / Inert atmosphere

6: potassium carbonate / acetonitrile / 12 h / 70 °C / Inert atmosphere

7: potassium carbonate; dichloromethane; Dess-Martin periodane / 1 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloromethane; 5%-palladium/activated carbon; water; hydrogen; boron trichloride; potassium carbonate; Dess-Martin periodane; potassium bromide; In 1,4-dioxane; dichloromethane; ethyl acetate; acetonitrile; 1: |Diels-Alder Cycloaddition / 7: |Dess-Martin Oxidation;

DOI:10.1021/ol303390a

Reference yield:

4-chloro-2(H)-pyran-2-one (129660-02-2) → 3-(2-(2,6-dimethoxy-5-((2-oxo-2H-pyran-4-yl)oxy)-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propanal (1417802-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / acetonitrile / 12 h / 70 °C / Inert atmosphere

2: potassium carbonate; dichloromethane; Dess-Martin periodane / 1 h / 20 °C / Inert atmosphere

With dichloromethane; potassium carbonate; Dess-Martin periodane; In acetonitrile; 2: |Dess-Martin Oxidation;

DOI:10.1021/ol303390a

upstream raw materials:

5'-(benzyloxy)-2-isopropoxy-3,4'-dimethoxy-2',6-divinyl-1,1'-biphenyl

4-chloro-2(H)-pyran-2-one

C₂₂H₃₉BO₄Si

tert-butyl(3-(2-(5-isopropoxy-2,6-dimethoxy-9,10-dihydrophenanthren-3-yl)-5-methoxyphenyl)propoxy)dimethylsilane

Downstream raw materials:

(E)-4-((3,7-dimethoxy-6-(4-methoxy-2-(4-(phenylsulfonyl)but-3-en-1-yl)phenyl)-9,10-dihydrophenanthren-4-yl)oxy)-2H-pyran-2-one

4-((6-(2-(but-3-yn-1-yl)-4-methoxyphenyl)-3,7-dimethoxy-9,10-dihydrophenanthren-4-yl)oxy)-2H-pyran-2-one

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