(1S,3R,5Z,7E,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10⁽¹⁹⁾-trien-1-yl tert-butyl(dimethyl)silyl ether

Base Information

• Chemical Name: (1S,3R,5Z,7E,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10⁽¹⁹⁾-trien-1-yl tert-butyl(dimethyl)silyl ether
• CAS No.: 488124-31-8
• Molecular Formula: C₄₁H₇₀O₄Si₂
• Molecular Weight: 683.175

Synonyms:(1S,3R,5Z,7E,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10⁽¹⁹⁾-trien-1-yl tert-butyl(dimethyl)silyl ether

Chemical Property of (1S,3R,5Z,7E,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10⁽¹⁹⁾-trien-1-yl tert-butyl(dimethyl)silyl ether

Chemical Property:

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Technology Process of (1S,3R,5Z,7E,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10⁽¹⁹⁾-trien-1-yl tert-butyl(dimethyl)silyl ether

There total 8 articles about (1S,3R,5Z,7E,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10⁽¹⁹⁾-trien-1-yl tert-butyl(dimethyl)silyl ether 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%

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) + (3aS,5aR,9aR)-3a,4,5,5a,8,9-hexahydro-3-[(1E)-4-(methoxymethoxy)-4-methylpent-1-enyl]-1H-cyclopenta[c]inden-6(7H)-one (488124-32-9) → (1S,3R,5Z,7E,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10(19)-trien-1-yl tert-butyl(dimethyl)silyl ether (488124-31-8)

Guidance literature:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

(3aS,5aR,9aR)-3a,4,5,5a,8,9-hexahydro-3-[(1E)-4-(methoxymethoxy)-4-methylpent-1-enyl]-1H-cyclopenta[c]inden-6(7H)-one; In tetrahydrofuran; hexane; at -78 - -40 ℃;

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

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,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10(19)-trien-1-yl tert-butyl(dimethyl)silyl ether (488124-31-8)

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: 66 percent / LiCl; Pd(Ph₃P)4 / tetrahydrofuran / 4 h / 75 °C

7.1: nBuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

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

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

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,22E)-3-[tert-butyl(dimethyl)silyl]oxy-20,21,22,23-tetrahydro-25-(methoxymethoxy)-18,21-cyclo-9,19-secocholesta-5,7,10(19)-trien-1-yl tert-butyl(dimethyl)silyl ether (488124-31-8)

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: 66 percent / LiCl; Pd(Ph₃P)4 / tetrahydrofuran / 4 h / 75 °C

8.1: nBuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

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

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

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

upstream raw materials:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(3aS,5aR,9aR)-3a,4,5,5a,8,9-hexahydro-3-[(1E)-4-(methoxymethoxy)-4-methylpent-1-enyl]-1H-cyclopenta[c]inden-6(7H)-one

(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

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