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

Base Information

• Chemical Name: (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene
• CAS No.: 147125-06-2
• Molecular Formula: C₃₄H₆₁IO₂Si₂
• Molecular Weight: 684.933
• Mol file: 147125-06-2.mol

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

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

There total 6 articles about (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-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: 87.0%

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (128387-35-9) → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (147125-06-2)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1021/jo00125a051

Reference yield: 66.0%

C34H62O5SSi2 → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (147125-06-2)

Guidance literature:

C₃₄H₆₂O₅SSi₂; With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 20 ℃; for 3h;

With sodium hydrogencarbonate; In ethanol; at 90 ℃; for 2h;

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) → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (147125-06-2)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; sodium tetrahydroborate; iodine; sodium hydrogencarbonate; ozone; triphenylphosphine; In ethanol; dichloromethane;

DOI:10.1021/jo00125a051

upstream raw materials:

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

(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

C₄₀H₇₂O₂Si₂

Downstream 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

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

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

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