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

Base Information

• Chemical Name: 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene
• CAS No.: 167892-92-4
• Molecular Formula: C₂₉H₄₇NOSi
• Molecular Weight: 453.784
• Mol file: 167892-92-4.mol

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

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

There total 1 articles about 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-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: 70.0%

potassium cyanide (151-50-8) + (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)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-92-4)

Guidance literature:

In dimethyl sulfoxide; at 90 ℃; for 0.5h;

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

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:

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-92-4) → 26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-1α,3β,25-triol

Guidance literature:

Multi-step reaction with 8 steps

1: 54 percent / DIBALH / tetrahydrofuran; hexane / -70 - 20 °C

2: 54 percent / diethyl ether / 0.17 h / 20 °C

3: 78 percent / TPAP; NMO; 4A MS / CH₂Cl₂ / 0.25 h / 20 °C

4: 41 percent / SeO₂ / CH₂Cl₂; methanol / 2 h / Heating

5: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C

6: 72 percent / Et₃N; anthracene / toluene / 1 h / Irradiation

7: 92 percent / LiN(TMS)2 / tetrahydrofuran; hexane / 0.17 h / -78 °C

8: 87 percent / MsOH / methanol / 1 h / 20 °C

With 1H-imidazole; selenium(IV) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonic acid; anthracene; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Reduction / 2: Grignard reaction / 3: Oxidation / 4: Oxidation / 5: Substitution / 6: Isomerization / 7: Condensation / 8: desilylation;

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

upstream raw materials:

potassium cyanide

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

Downstream raw materials:

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

ST₂₃₂

(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

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