(5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10⁽¹⁹⁾,20-tetraene

Base Information

• Chemical Name: (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10⁽¹⁹⁾,20-tetraene
• CAS No.: 442200-75-1
• Molecular Formula: C₃₉H₇₀O₃Si₂
• Molecular Weight: 643.154

Synonyms:(5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10⁽¹⁹⁾,20-tetraene

Chemical Property of (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10⁽¹⁹⁾,20-tetraene

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Technology Process of (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10⁽¹⁹⁾,20-tetraene

There total 8 articles about (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10⁽¹⁹⁾,20-tetraene 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: 86.0%

methyllithium (917-54-4) + (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-[2-(methoxycarbonyl)ethyl]-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene (442200-74-0) → (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene (442200-75-1)

Guidance literature:

In tetrahydrofuran; hexane; at -78 - -10 ℃;

DOI:10.1021/jo020022z

Reference yield:

(8β,20ξ)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-pregnan-20-ol → (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene (442200-75-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (diacetoxyiodo)benzene; I₂ / cyclohexane / 15 h / UV-irradiation

2.1: 702 mg / Jones's reagent / acetone / 2 h / 0 °C

3.1: 40 percent / Zn; CuI / aq. ethanol / 4 h / sonication

4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 20 °C

4.2: 80 percent / tetrahydrofuran; hexane / 20 h

5.1: 87 percent / TBAF / tetrahydrofuran / 22 h / Heating

6.1: 88 percent / PDC / CH₂Cl₂ / 6 h

7.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

7.2: 65 percent / tetrahydrofuran; hexane / -78 - -50 °C

8.1: 86 percent / tetrahydrofuran; hexane / -78 - -10 °C

With copper(l) iodide; dipyridinium dichromate; n-butyllithium; [bis(acetoxy)iodo]benzene; Jones's reagent; tetrabutyl ammonium fluoride; iodine; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; cyclohexane; acetone; 2.1: Jones oxidation / 4.1: Wittig reaction / 4.2: Wittig reaction / 7.1: Wittig-Horner reaction / 7.2: Wittig-Horner reaction;

DOI:10.1021/jo020022z

Reference yield:

des-A,B-18-[2-(methoxycarbonyl)ethyl]-20-methylpregn-20-en-8-one (442200-73-9) → (5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-(3-hydroxy-3-methylbutyl)-20-methyl-9,10-secopregna-5,7,10(19),20-tetraene (442200-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 65 percent / tetrahydrofuran; hexane / -78 - -50 °C

2.1: 86 percent / tetrahydrofuran; hexane / -78 - -10 °C

With n-butyllithium; In tetrahydrofuran; hexane; 1.1: Wittig-Horner reaction / 1.2: Wittig-Horner reaction;

DOI:10.1021/jo020022z

upstream raw materials:

methyllithium

(5Z,7E)-(1S,3R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18-[2-(methoxycarbonyl)ethyl]-20-methyl-9,10-secopregna-5,7,10⁽¹⁹⁾,20-tetraene

des-A,B-18-[2-(methoxycarbonyl)ethyl]-20-methylpregn-20-en-8-one

(8β)-des-A,B-18-[2-(methoxycarbonyl)ethyl]-20-methylpregn-20-en-8-ol

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