(1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾-trien-25-ol

Base Information

• Chemical Name: (1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾-trien-25-ol
• CAS No.: 488124-29-4
• Molecular Formula: C₃₉H₆₄O₃Si₂
• Molecular Weight: 637.106

Synonyms:(1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾-trien-25-ol

Chemical Property of (1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾-trien-25-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾-trien-25-ol

There total 7 articles about (1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾-trien-25-ol 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:

(3aS,5aR,6S,9aR)-3a,4,5,5a,6,7,8,9-octahydro-6-hydroxycyclopenta[c]inden-3(3H)-one (488124-20-5) → (1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10(19)-trien-25-ol (488124-29-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 66 percent / imidazole / dimethylformamide / 24 h / 60 °C

2.1: 100 percent / hydrogen / Pd/C (5 percent) / ethyl acetate / 2 h

3.1: LDA / tetrahydrofuran / 2 h / -78 °C

3.2: 86 percent / tetrahydrofuran / -78 - 20 °C

4.1: 96 percent / HF (48 percent) / acetonitrile / 2 h

5.1: 100 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

6.1: 92 percent / Pd(Ph₃P)4; pyrrolidine / 0.5 h

7.1: nBuLi / tetrahydrofuran; hexane / -78 - -40 °C

7.2: 86 percent / tetrahydrofuran; hexane / -78 - -40 °C

With pyrrolidine; 1H-imidazole; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 7.2: Wittig-Horner coupling;

DOI:10.1002/1522-2675(200210)85:10<3251::AID-HLCA3251>3.0.CO;2-Z

Reference yield:

(1S,4S,7R,8S,12S)-3-methyl-2,13-dioxatetracyclo[6.5.0.04,8.07,12]tridecan-3-ol (488124-22-7) → (1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10(19)-trien-25-ol (488124-29-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: t-BuOK / tetrahydrofuran

2.1: 66 percent / imidazole / dimethylformamide / 24 h / 60 °C

3.1: 100 percent / hydrogen / Pd/C (5 percent) / ethyl acetate / 2 h

4.1: LDA / tetrahydrofuran / 2 h / -78 °C

4.2: 86 percent / tetrahydrofuran / -78 - 20 °C

5.1: 96 percent / HF (48 percent) / acetonitrile / 2 h

6.1: 100 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

7.1: 92 percent / Pd(Ph₃P)4; pyrrolidine / 0.5 h

8.1: nBuLi / tetrahydrofuran; hexane / -78 - -40 °C

8.2: 86 percent / tetrahydrofuran; hexane / -78 - -40 °C

With pyrrolidine; 1H-imidazole; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; hydrogen fluoride; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 8.2: Wittig-Horner coupling;

DOI:10.1002/1522-2675(200210)85:10<3251::AID-HLCA3251>3.0.CO;2-Z

Reference yield:

(1S,3aR,4S,7aS)-2,3,3a,4,5,6,7,7a-octahydro-7a-methyl-1-(2-methyl-1,3-dioxolan-2-yl)inden-4(1H)-ol → (1S,3R,5Z,7E)-1,3-bis{[(tert-butyl)dimethylsilyl]oxy}-20,21,22,22,23,23-hexahydro-18,21-cyclo-9,10-secocholesta-5,7,10(19)-trien-25-ol (488124-29-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CaCO₃; I₂ / cyclohexane / 3 h / Irradiation

1.2: pyridinium p-toluenesulfonate / acetone; H₂O / 2 h / Heating

2.1: t-BuOK / tetrahydrofuran

3.1: 66 percent / imidazole / dimethylformamide / 24 h / 60 °C

4.1: 100 percent / hydrogen / Pd/C (5 percent) / ethyl acetate / 2 h

5.1: LDA / tetrahydrofuran / 2 h / -78 °C

5.2: 86 percent / tetrahydrofuran / -78 - 20 °C

6.1: 96 percent / HF (48 percent) / acetonitrile / 2 h

7.1: 100 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

8.1: 92 percent / Pd(Ph₃P)4; pyrrolidine / 0.5 h

9.1: nBuLi / tetrahydrofuran; hexane / -78 - -40 °C

9.2: 86 percent / tetrahydrofuran; hexane / -78 - -40 °C

With pyrrolidine; 1H-imidazole; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; hydrogen fluoride; potassium tert-butylate; hydrogen; iodine; pyridinium p-toluenesulfonate; calcium carbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 9.2: Wittig-Horner coupling;

DOI:10.1002/1522-2675(200210)85:10<3251::AID-HLCA3251>3.0.CO;2-Z

upstream raw materials:

2-methylpent-4-yn-2-ol

(3aS,5aR,6S,9aR)-3a,4,5,5a,6,7,8,9-octahydro-6-hydroxycyclopenta[c]inden-3(3H)-one

(1S,4S,7R,8S,12S)-3-methyl-2,13-dioxatetracyclo[6.5.0.0^4,8.0^7,12]tridecan-3-ol

(3aS,5aR,6S,9aR)-6-{[(tert-butyl)(dimethyl)silyl]oxy}-3a,4,5,5a,6,7,8,9-octahydrocyclopenta[c]inden-3(3H)-one

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