17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene-3,4-dione

Base Information

• Chemical Name: 17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopenta
• Molecular Formula: C₃₃H₃₀O₃Si
• Molecular Weight: 502.685

Synonyms:17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene-3,4-dione

Chemical Property of 17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopenta

Chemical Property:

Purity/Quality:

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Useful:

There total 6 articles about 17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene-3,4-dione 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: 72.0%

17-(tert-Butyl-diphenyl-silanyloxy)-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol (150711-22-1) → 17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene-3,4-dione (145629-00-1)

Guidance literature:

With potassium dihydrogenphosphate; adogen 464; potassium nitrososulfonate; In benzene;

DOI:10.1021/jo00054a018

Reference yield:

3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one (792-07-4) → 17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene-3,4-dione (145629-00-1)

Guidance literature:

Multi-step reaction with 6 steps

1: BBr₃ / CH₂Cl₂ / 1.5 h / -78 °C

2: 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h

3: 83 percent / NaBH₄ / tetrahydrofuran; methanol / 2.5 h / Ambient temperature

4: 81 percent / 4-(N,N-dimethylamino)pyridine, imidazole / CH₂Cl₂ / 2 h / Ambient temperature

5: 100 percent / 0.1 M KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

6: 72 percent / (SO₃K)2NO, KH₂PO₄, Adogen 464 / benzene

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; potassium dihydrogenphosphate; adogen 464; potassium nitrososulfonate; boron tribromide; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00054a018

Reference yield:

15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one (24684-50-2) → 17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene-3,4-dione (145629-00-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h

2: 83 percent / NaBH₄ / tetrahydrofuran; methanol / 2.5 h / Ambient temperature

3: 81 percent / 4-(N,N-dimethylamino)pyridine, imidazole / CH₂Cl₂ / 2 h / Ambient temperature

4: 100 percent / 0.1 M KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

5: 72 percent / (SO₃K)2NO, KH₂PO₄, Adogen 464 / benzene

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; potassium dihydrogenphosphate; adogen 464; potassium nitrososulfonate; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00054a018

upstream raw materials:

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

3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one

15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one

3-(Benzoyloxy)-15,16-dihydrocyclopentaphenanthren-17-one

Downstream raw materials:

3,4,15,16-tetrahydro-trans-3,4-dihydroxycyclopentaphenanthren-17-one

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