1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene

Base Information

• Chemical Name: 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene
• CAS No.: 167892-97-9
• Molecular Formula: C₃₆H₆₄O₃Si₂
• Molecular Weight: 601.073
• Mol file: 167892-97-9.mol

Synonyms:1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene

Chemical Property of 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene

There total 6 articles about 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),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: 89.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1α-hydroxy-3β-[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-96-8) → 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-97-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/S0968-0896(00)00106-1

Reference yield:

(5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene (143884-24-6) → 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-97-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / dimethylsulfoxide / 0.5 h / 90 °C

2: 54 percent / DIBALH / tetrahydrofuran; hexane / -70 - 20 °C

3: 54 percent / diethyl ether / 0.17 h / 20 °C

4: 78 percent / TPAP; NMO; 4A MS / CH₂Cl₂ / 0.25 h / 20 °C

5: 41 percent / SeO₂ / CH₂Cl₂; methanol / 2 h / Heating

6: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; selenium(IV) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Substitution / 2: Reduction / 3: Grignard reaction / 4: Oxidation / 5: Oxidation / 6: Substitution;

DOI:10.1016/S0968-0896(00)00106-1

Reference yield:

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-93-5) → 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-97-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 54 percent / diethyl ether / 0.17 h / 20 °C

2: 78 percent / TPAP; NMO; 4A MS / CH₂Cl₂ / 0.25 h / 20 °C

3: 41 percent / SeO₂ / CH₂Cl₂; methanol / 2 h / Heating

4: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; selenium(IV) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Grignard reaction / 2: Oxidation / 3: Oxidation / 4: Substitution;

DOI:10.1016/S0968-0896(00)00106-1

upstream raw materials:

tert-butyldimethylsilyl chloride

1α-hydroxy-3β-[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene

(5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene

Downstream raw materials:

1α,3β-bis[(t-butyldimethylsilyl)oxy]-23(R)-[(methanesulfonyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

1α,3β-bis[(t-butyldimethylsilyl)oxy]-23(S)-[(methanesulfonyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-trien-23(R),25-diol

1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-trien-23(S),25-diol