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

Base Information

• Chemical Name: 1(S),3(R)-bis[(tert-butyldimethylsilyl)oxy]-25-keto-9,10-seco-27-norcholesta-5(Z),7(E),10⁽¹⁹⁾triene
• CAS No.: 398457-49-3
• Molecular Formula: C₃₈H₆₈O₃Si₂
• Molecular Weight: 629.127

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

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

Chemical Property:

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

There total 2 articles about 1(S),3(R)-bis[(tert-butyldimethylsilyl)oxy]-25-keto-9,10-seco-27-norcholesta-5(Z),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: 71.0%

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene (147125-20-0) → 1(S),3(R)-bis[(tert-butyldimethylsilyl)oxy]-25-keto-9,10-seco-27-norcholesta-5(Z),7(E),10(19)triene (398457-49-3)

Guidance literature:

With 9-acetylanthracene; triethylamine; In toluene; at 10 ℃; for 0.25h; Irradiation;

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

Reference yield:

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (147125-06-2) → 1(S),3(R)-bis[(tert-butyldimethylsilyl)oxy]-25-keto-9,10-seco-27-norcholesta-5(Z),7(E),10(19)triene (398457-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NiCl₂*6H₂O; Zn; pyridine / 0.5 h / 65 °C

1.2: 53 percent / pyridine / tetrahydrofuran / 2 h / 20 °C

2.1: 71 percent / 9-acetylanthracene; Et₃N / toluene / 0.25 h / 10 °C / Irradiation

With pyridine; 9-acetylanthracene; triethylamine; nickel dichloride; zinc; In toluene;

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

Reference yield:

[11C]methyl iodide (54245-42-0) + 1(S),3(R)-bis[(tert-butyldimethylsilyl)oxy]-25-keto-9,10-seco-27-norcholesta-5(Z),7(E),10(19)triene (398457-49-3) → C38(11)CH72O3Si2

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -70 - -10 ℃; for 0.166667h;

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

upstream raw materials:

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

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