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

Base Information

• Chemical Name: 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
• CAS No.: 134404-39-0
• Molecular Formula: C₃₇H₆₄O₄Si₂
• Molecular Weight: 629.084

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 2 articles about 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 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: 70.8%

trimethyl phosphonoacetate (5927-18-4) + (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) → 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)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 1h;

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) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 94.7 percent / anthracene; triethylamine / 0.5 h / Irradiation

2: 70.8 percent / sodium hydride / tetrahydrofuran / 1 h

With anthracene; sodium hydride; triethylamine; In tetrahydrofuran;

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

Reference yield: 77.1%

diisopropyl methanephosphonate (1445-75-6) + 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) → bis(1-methylethyl) [(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 (227747-71-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

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

upstream raw materials:

trimethyl phosphonoacetate

(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)-(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

bis(1-methylethyl) [(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

dimethyl [(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

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

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