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

Base Information

• Chemical Name: 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
• CAS No.: 227747-87-7
• Molecular Formula: C₄₆H₈₆O₈P₂Si₂
• Molecular Weight: 885.303

Synonyms: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

Chemical Property of 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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Technology Process of 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

There total 7 articles about 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 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: 61.9%

Diethyl methylphosphonate (683-08-9) + 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) → 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 (227747-87-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 24h;

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

Reference yield:

Tetraethyl methylenediphosphonate (1660-94-2) → 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 (227747-87-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 61.9 percent / n-butyllithium / tetrahydrofuran; hexane / 24 h / -78 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane;

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,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 (227747-87-7)

Guidance literature:

Multi-step reaction with 5 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

5: 61.9 percent / n-butyllithium / tetrahydrofuran; hexane / 24 h / -78 °C

With n-butyllithium; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; toluene;

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

upstream raw materials:

Diethyl methylphosphonate

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 methylenediphosphonate

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

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