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

Base Information

• Chemical Name: 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene
• CAS No.: 167892-93-5
• Molecular Formula: C₂₉H₄₈O₂Si
• Molecular Weight: 456.784
• Mol file: 167892-93-5.mol

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

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

There total 2 articles about 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-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: 54.0%

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-92-4) → 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-93-5)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -70 - 20 ℃;

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) → 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-93-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; dimethyl sulfoxide; 1: Substitution / 2: Reduction;

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

Reference yield: 54.0%

methylmagnesium bromide (75-16-1) + 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-93-5) → (R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol (167892-94-6)

Guidance literature:

In diethyl ether; at 20 ℃; for 0.166667h;

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

upstream raw materials:

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-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

Downstream raw materials:

(R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol

ST₂₃₂

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

23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-1α,3β,25-triol