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

Base Information

• Chemical Name: 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
• CAS No.: 227747-89-9
• Molecular Formula: C₄₅H₈₂O₈P₂Si₂
• Molecular Weight: 869.26

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of 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

There total 5 articles about 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 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: 55.5%

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) → 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 (227747-89-9)

Guidance literature:

With 4-methyl-morpholine; tetrachloromethane; titanium tetrachloride; In tetrahydrofuran; at 20 ℃;

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) → 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 (227747-89-9)

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: 55.5 percent / titanium(IV) chloride; N-methylmorpholine; tetrachloromethane / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; tetrachloromethane; titanium tetrachloride; 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) → 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 (227747-89-9)

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: 55.5 percent / titanium(IV) chloride; N-methylmorpholine; tetrachloromethane / tetrahydrofuran / 20 °C

With 4-methyl-morpholine; tetrachloromethane; anthracene; titanium tetrachloride; 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

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