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

Base Information

• Chemical Name: diethyl [(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-24a-yl]phosphonate
• CAS No.: 227747-67-3
• Molecular Formula: C₄₁H₇₃O₆PSi₂
• Molecular Weight: 749.172

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about diethyl [(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10⁽¹⁹⁾,22-tetraen-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: 73.8%

Diethyl methylphosphonate (683-08-9) + methyl (5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9,10-secochola-5,7,10(19),22-tetraen-24-oate (134404-39-0) → diethyl [(5Z,7E,22E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl]phosphonate (227747-67-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; 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)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl]phosphonate (227747-67-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 73.8 percent / n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

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

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)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl]phosphonate (227747-67-3)

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: 73.8 percent / n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

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

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

upstream raw materials:

Diethyl methylphosphonate

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

(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:

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

((E)-(R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-hydroxy-hex-3-enyl)-phosphonic acid diethyl ester

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