(3beta,4alpha)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}gona-1,5(10),6,8,11,13-hexaen-17-one

Base Information

• Chemical Name: (3beta,4alpha)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}gona-1,5(10),6,8,11,13-hexaen-17-one
• CAS No.: 143216-83-5
• Molecular Formula: C₂₉H₄₂O₃Si₂
• Molecular Weight: 494.822
• Mol file: 143216-83-5.mol

Synonyms:17H-Cyclopenta[a]phenanthren-17-one,3,4-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,4,15,16-tetrahydro-, trans-(9CI); 17H-Cyclopenta[a]phenanthren-17-one,3,4-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,4,15,16-tetrahydro-, trans-(?à)-

Chemical Property of (3beta,4alpha)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}gona-1,5(10),6,8,11,13-hexaen-17-one

Chemical Property:

• Vapor Pressure: 1.17E-11mmHg at 25°C
• Boiling Point: 538.3°C at 760 mmHg
• Flash Point: 232°C
• Density: 1.05g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3beta,4alpha)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}gona-1,5(10),6,8,11,13-hexaen-17-one

There total 7 articles about (3beta,4alpha)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}gona-1,5(10),6,8,11,13-hexaen-17-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: 52.0%

3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one methoxime (143216-82-4) → 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one (143216-83-5)

Guidance literature:

With titanium trichloride tris(tetrahydrofuran); diisobutylaluminium hydride; In toluene; for 18h;

DOI:10.1021/jo00047a030

Reference yield:

3-methoxy-6,7,16,17-tetrahydro-15H-cyclopenta-phenanthren-17-one (17521-83-4) → 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one (143216-83-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / 10percent Pd/C / various solvent(s) / 4 h / Heating

2: 95 percent / BBr₃ / CH₂Cl₂ / Ambient temperature

3: 92 percent / pyridine / 18 h

4: 77 percent / (PhSeO)2O / tetrahydrofuran / 4 h / Heating

5: NaBH₄, O₂ / ethanol / 96 h

6: Et₃N / benzene / 4 h / Ambient temperature

7: 52 percent / TiCl₃*3THF, DIBAL-H / toluene / 18 h

With pyridine; sodium tetrahydroborate; titanium trichloride tris(tetrahydrofuran); (PhSeO)2O; oxygen; boron tribromide; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; benzene;

DOI:10.1021/jo00047a030

Reference yield:

3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one (792-07-4) → 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one (143216-83-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / BBr₃ / CH₂Cl₂ / Ambient temperature

2: 92 percent / pyridine / 18 h

3: 77 percent / (PhSeO)2O / tetrahydrofuran / 4 h / Heating

4: NaBH₄, O₂ / ethanol / 96 h

5: Et₃N / benzene / 4 h / Ambient temperature

6: 52 percent / TiCl₃*3THF, DIBAL-H / toluene / 18 h

With pyridine; sodium tetrahydroborate; titanium trichloride tris(tetrahydrofuran); (PhSeO)2O; oxygen; boron tribromide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene; benzene;

DOI:10.1021/jo00047a030

upstream raw materials:

3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one methoxime

3-methoxy-6,7,16,17-tetrahydro-15H-cyclopenta-phenanthren-17-one

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

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

Downstream raw materials:

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

(+/-)-2α-bromo-1,2,3,4,15,16-hexahydro-trans-1β,3α,4β-trihydroxycyclopentaphenanthren-17-one