ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate

Base Information

• Chemical Name: ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate
• CAS No.: 147125-21-1
• Molecular Formula: C₃₉H₇₀O₄Si₂
• Molecular Weight: 659.153
• Mol file: 147125-21-1.mol

Synonyms:ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate

Chemical Property of ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate

There total 7 articles about ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate 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:

ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate (169900-32-7) → ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate (147125-21-1)

Guidance literature:

With 9-acetylanthracene; In hexane; at 0 - 5 ℃; for 0.75h; Irradiation;

DOI:10.1021/jo00125a051

Reference yield:

(6S)- and (6R)-SO2 adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (170081-46-6) → ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate (147125-21-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -10 deg C, 45 min, 2.) room temperature, 2 h

2: 47 percent / NaHCO₃ / aq. ethanol / 5 h / Heating

3: 87 percent / imidazole, PPh₃, I₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 77 percent / Zn, NiCl₂*6H₂O, I₂ / pyridine / 0.75 h / Ambient temperature

5: 915 mg / 9-acetylanthracene / hexane / 0.75 h / 0 - 5 °C / Irradiation

With 1H-imidazole; sodium tetrahydroborate; 9-acetylanthracene; iodine; sodium hydrogencarbonate; ozone; triphenylphosphine; nickel dichloride; zinc; In pyridine; ethanol; hexane; dichloromethane;

DOI:10.1021/jo00125a051

Reference yield:

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene SO2 adduct → ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate (147125-21-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 47 percent / NaHCO₃ / aq. ethanol / 5 h / Heating

2: 87 percent / imidazole, PPh₃, I₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 77 percent / Zn, NiCl₂*6H₂O, I₂ / pyridine / 0.75 h / Ambient temperature

4: 915 mg / 9-acetylanthracene / hexane / 0.75 h / 0 - 5 °C / Irradiation

With 1H-imidazole; 9-acetylanthracene; iodine; sodium hydrogencarbonate; triphenylphosphine; nickel dichloride; zinc; In pyridine; ethanol; hexane; dichloromethane;

DOI:10.1021/jo00125a051

upstream raw materials:

ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate

(6S)- and (6R)-SO₂ adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene

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

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

Downstream raw materials:

calcitriol

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol