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

Base Information

• Chemical Name: 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
• CAS No.: 227747-77-5
• Molecular Formula: C₄₁H₇₃O₅PSi₂
• Molecular Weight: 733.172

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 5 articles about 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 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: 58.2%

Tetraethyl methylenediphosphonate (1660-94-2) + (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) → 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 (227747-77-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

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) → 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 (227747-77-5)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 96.4 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h

4: 58.2 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

With sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;

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

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) → 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 (227747-77-5)

Guidance literature:

Multi-step reaction with 5 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

4: 96.4 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h

5: 58.2 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

With anthracene; sodium hydride; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;

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

upstream raw materials:

Tetraethyl methylenediphosphonate

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

(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:

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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