((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 diisopropyl ester

Base Information

• Chemical Name: ((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 diisopropyl ester
• CAS No.: 227747-73-1
• Molecular Formula: C₄₃H₇₉O₆PSi₂
• Molecular Weight: 779.241

Synonyms:((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 diisopropyl ester

Chemical Property of ((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 diisopropyl ester

Chemical Property:

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Technology Process of ((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 diisopropyl ester

There total 5 articles about ((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 diisopropyl ester 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: 93.7%

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) → ((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 diisopropyl ester (227747-73-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane; at 0 ℃; for 0.25h;

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

Reference yield:

diisopropyl methanephosphonate (1445-75-6) → ((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 diisopropyl ester (227747-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 77.1 percent / n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

2: 93.7 percent / cerium trichloride heptahydrate; sodium borohydride / methanol; CH₂Cl₂ / 0.25 h / 0 °C

With sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane;

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) → ((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 diisopropyl ester (227747-73-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 77.1 percent / n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3: 93.7 percent / cerium trichloride heptahydrate; sodium borohydride / methanol; CH₂Cl₂ / 0.25 h / 0 °C

With sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; sodium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane;

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

upstream raw materials:

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

diisopropyl methanephosphonate

(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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