(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene

Base Information

• Chemical Name: (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene
• CAS No.: 147125-20-0
• Molecular Formula: C₃₈H₆₈O₃Si₂
• Molecular Weight: 629.127
• Mol file: 147125-20-0.mol

Synonyms:(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene

Chemical Property of (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene

There total 9 articles about (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-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: 53.0%

methyl vinyl ketone (78-94-4,25038-87-3) + (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (147125-06-2) → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene (147125-20-0)

Guidance literature:

methyl vinyl ketone; With pyridine; nickel dichloride; zinc; at 65 ℃; for 0.5h;

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene; With pyridine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(01)00178-X

Reference yield: 34.8%

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-6-{(1R,3aS,7aR)-4-[2-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-heptan-2-one → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene (147125-20-0) + (R)-6-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-heptan-2-one

Guidance literature:

With 1H-imidazole; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00125a051

Reference yield:

Calciferol (50-14-6) → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene (147125-20-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) SO₂

2: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -10 deg C, 2.) room temperature, 2 h

3: 71 percent / I₂, PPh₃, imidazole / CH₂Cl₂ / 1.) 5 deg C, 0.5 h, 2.) room temperature, 2.0 h

4: Zn, NiCl₂*6H₂O / pyridine; tetrahydrofuran / 1.) 65 deg C, 30 min, 2.) room temperature, 2.0 h

5: NaHCO₃ / aq. ethanol / 2 h / Heating

6: 2.4 g / SeO₂, N-methylmorpholine N-oxide / methanol; CH₂Cl₂ / 2 h / Heating

7: 34.8 percent / imidazole / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; selenium(IV) oxide; sulfur dioxide; iodine; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; nickel dichloride; zinc; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane;

DOI:10.1021/jo00125a051

upstream raw materials:

tert-butyldimethylsilyl chloride

methyl vinyl ketone

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene

Calciferol

Downstream raw materials:

1(S),3(R)-bis[(tert-butyldimethylsilyl)oxy]-25-keto-9,10-seco-27-norcholesta-5(Z),7(E),10⁽¹⁹⁾triene