(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24-ol

Base Information

• Chemical Name: (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24-ol
• CAS No.: 134404-40-3
• Molecular Formula: C₃₆H₆₄O₃Si₂
• Molecular Weight: 601.073

Synonyms:(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24-ol

Chemical Property of (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24-ol

There total 2 articles about (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24-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:

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al (112828-13-4) → (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-ol (134404-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 94.7 percent / anthracene; triethylamine / 0.5 h / Irradiation

2: 70.8 percent / sodium hydride / tetrahydrofuran / 1 h

3: 76.8 percent / diisobutylaluminum hydride / toluene / 0.5 h / -23 °C

With anthracene; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1016/S0039-128X(00)00148-3

Reference yield:

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-al (112924-91-1) → (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-ol (134404-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70.8 percent / sodium hydride / tetrahydrofuran / 1 h

2: 76.8 percent / diisobutylaluminum hydride / toluene / 0.5 h / -23 °C

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1016/S0039-128X(00)00148-3

Reference yield: 96.4%

(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-ol (134404-40-3) → (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-al (134404-41-4)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 3h;

DOI:10.1016/S0039-128X(00)00148-3

upstream raw materials:

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-al

(5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al

Downstream raw materials:

(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24-al

diethyl (5Z,7E,22E,24E)-(1S,3R)-[1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24a-homo-9,10-secochola-5,7,10⁽¹⁹⁾,22,24-pentaen-24a-yl]phosphonate

tetraethyl (5Z,7E,22E)-(1S,3R)-[1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24a-homo-9,10-secochola-5,7,10⁽¹⁹⁾,22,24-pentaene-24a,24a-diyl]bisphosphonate

tetraethyl (5Z,7E,22E,24E)-(1S,3R)-[1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-nor-9,10-secocholesta-5,7,10⁽¹⁹⁾,22-tetraene-26,27-diyl]bisphosphonate

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