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

Base Information

• Chemical Name: 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
• CAS No.: 227747-75-3
• Molecular Formula: C₄₅H₈₂O₉P₂Si₂
• Molecular Weight: 885.259

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 81.2%

diethyl chlorophosphate (814-49-3) + 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) → 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 (227747-75-3)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; at 0 ℃; for 1h;

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

Reference yield:

Diethyl methylphosphonate (683-08-9) → 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 (227747-75-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 81.2 percent / diisopropylamine; n-butyllithium / tetrahydrofuran / 1 h / 0 °C

With n-butyllithium; diisopropylamine; 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) → 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 (227747-75-3)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 81.2 percent / diisopropylamine; n-butyllithium / tetrahydrofuran / 1 h / 0 °C

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

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

upstream raw materials:

diethyl chlorophosphate

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

Diethyl methylphosphonate

(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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