3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene

Base Information

• Chemical Name: 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydrocyclopenta
• Molecular Formula: C₄₀H₃₆O₃Si
• Molecular Weight: 592.81

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

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

Chemical Property:

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There total 4 articles about 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene 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: 81.0%

Benzoic acid 17-hydroxy-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-yl ester (145628-94-0) + tert-butylchlorodiphenylsilane (58479-61-1) → 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene (145628-96-2)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo00054a018

Reference yield:

3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one (792-07-4) → 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene (145628-96-2)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; dmap; sodium tetrahydroborate; boron tribromide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00054a018

Reference yield:

15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one (24684-50-2) → 3-(Benzoyloxy)-17-<(tert-butyldiphenylsilyl)oxy>-15,16-dihydrocyclopentaphenanthrene (145628-96-2)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; dmap; sodium tetrahydroborate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00054a018

upstream raw materials:

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

tert-butylchlorodiphenylsilane

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

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

Downstream raw materials:

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

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

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

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