1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene

Base Information

• Chemical Name: 1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene
• CAS No.: 263712-17-0
• Molecular Formula: C₃₉H₇₂O₂Si₂
• Molecular Weight: 637.139
• Mol file: 263712-17-0.mol

Synonyms:

Chemical Property of 1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene

There total 7 articles about 1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene 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: 17.0%

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) + De-A,B-[22,22,23,23-3H4]-8-oxocholestane (263712-16-9) → 1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene (263712-17-0)

Guidance literature:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With n-butyllithium; In tetrahydrofuran; at -75 ℃; for 0.0833333h;

De-A,B-[22,22,23,23-3H₄]-8-oxocholestane; In tetrahydrofuran; at -75 - 20 ℃; for 1.16667h;

DOI:10.1248/cpb.48.215

Reference yield:

(S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal (104651-47-0) → 1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene (263712-17-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / PPh₃ / CH₂Cl₂ / 0.05 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

2.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.1: pyridine / CH₂Cl₂ / 2 h / 20 °C

4.1: 98 percent / n-Bu₃SnH; 2,2-azabisisobutyronitrile / toluene / 3 h / Heating

5.1: 68 percent / 6N HCl / tetrahydrofuran / 7 h / Heating

6.1: 56 percent / PCC; Celite / CH₂Cl₂ / 1.5 h / 20 °C

7.1: T₂ / 10 percent Pd/C / ethyl acetate / 3 h / 20 °C

8.1: n-BuLi / tetrahydrofuran / 0.08 h / -75 °C

8.2: 17 percent / tetrahydrofuran / 1.17 h / -75 - 20 °C

With pyridine; hydrogenchloride; n-butyllithium; tritium; 2,2'-azobis(isobutyronitrile); Celite; tri-n-butyl-tin hydride; triphenylphosphine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; toluene;

DOI:10.1248/cpb.48.215

Reference yield:

(8β)-De-A,B-22-cholestyne-8-one (263712-15-8) → 1α,3β-bis(tert-butyldimethylsilyloxy)-[22,22,23,23-3H4]-9,10-secocholesta-5,7,10(19)-triene (263712-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: T₂ / 10 percent Pd/C / ethyl acetate / 3 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / 0.08 h / -75 °C

2.2: 17 percent / tetrahydrofuran / 1.17 h / -75 - 20 °C

With n-butyllithium; tritium; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1248/cpb.48.215

upstream raw materials:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

De-A,B-[22,22,23,23-3H₄]-8-oxocholestane

(S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal

(8β)-De-A,B-22-cholestyne-8-one

Refernces