3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene

Base Information

• Chemical Name: 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopenta
• Molecular Formula: C₄₁H₃₈O₃Si
• Molecular Weight: 606.836

Synonyms:3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene

Chemical Property of 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopenta

Chemical Property:

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There total 8 articles about 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene 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: 85.0%

Benzoic acid 17-hydroxy-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-yl ester (145628-95-1) + tert-butylchlorodiphenylsilane (58479-61-1) → 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene (145628-97-3)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; for 5h; Ambient temperature;

DOI:10.1021/jo00054a018

Reference yield:

3-Methoxy-11-methyl-6,7,15,16-tetrahydrocyclopentaphenanthrene (145628-87-1) → 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene (145628-97-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetic acid; H₂O / 24 h / Ambient temperature

2: 75 percent / 10 percent Pd/C / various solvent(s) / 1 h / Heating

3: BBr₃ / CH₂Cl₂ / 2 h / -78 °C

4: pyridine / 5 h

5: 95 percent / NaBH₄ / tetrahydrofuran; methanol / Ambient temperature

6: 85 percent / 4-(N,N-dimethylamino)pyridine, imidazole / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; boron tribromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid;

DOI:10.1021/jo00054a018

Reference yield:

15,16-Dihydro-3-methoxy-11-methylcyclopentaphenanthrene (145627-72-1) → 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene (145628-97-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 64 percent / H₂ / 10 percent Pd/C / ethyl acetate / 16 h / 1654.9 Torr

2: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetic acid; H₂O / 24 h / Ambient temperature

3: 75 percent / 10 percent Pd/C / various solvent(s) / 1 h / Heating

4: BBr₃ / CH₂Cl₂ / 2 h / -78 °C

5: pyridine / 5 h

6: 95 percent / NaBH₄ / tetrahydrofuran; methanol / Ambient temperature

7: 85 percent / 4-(N,N-dimethylamino)pyridine, imidazole / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen; boron tribromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate;

DOI:10.1021/jo00054a018

upstream raw materials:

Benzoic acid 17-hydroxy-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-yl ester

tert-butylchlorodiphenylsilane

benzoyl chloride

15,16-Dihydro-3-methoxy-11-methylcyclopentaphenanthrene

Downstream raw materials:

trans-3,4-Dihydroxy-15,16-dihydro-11-methylcyclopentaphenanthren-17-one

17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene-3,4-dione

17-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol

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