(6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol

Base Information

• Chemical Name: (6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol
• CAS No.: 501431-59-0
• Molecular Formula: C₄₇H₈₄O₃Si₂
• Molecular Weight: 753.353

Synonyms:(6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol

Chemical Property of (6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol

There total 10 articles about (6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol 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: 52.0%

(5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a-homo-26,27-di-n-propyl-9,10-secocholesta-5,7,10(19),24-tetraen-23,25-diol (501431-55-6) → (6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol (501431-59-0)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0039-128X(02)00038-7

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol (501431-59-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: 97 percent / sodium borohydride / CH₂Cl₂; methanol / 0.25 h / 20 °C

3.1: 60 percent / KOH / methanol / 48 h / 95 °C

4.1: 90 percent / triethylamine; 4,4-dimethylaminopyridine / CH₂Cl₂ / 28 h / 20 °C

5.1: lithium bromide dihydrate; lithium carbonate / dimethylformamide / 0.33 h / 80 °C

5.2: 88 percent / dimethylformamide / 2.5 h / 80 °C

6.1: 88 percent / n-BuLi / tetrahydrofuran / 0.25 h / -70 °C

7.1: 41 percent / diethyl ether; tetrahydrofuran / 1 h / 0 °C

8.1: 52 percent / Na₂HPO₄; sodium amalgam / methanol / 2 h / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; lithium carbonate; triethylamine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(02)00038-7

Reference yield:

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrienol 22-p-toluenesulfonate (114694-13-2) → (6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol (501431-59-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium bromide dihydrate; lithium carbonate / dimethylformamide / 0.33 h / 80 °C

1.2: 88 percent / dimethylformamide / 2.5 h / 80 °C

2.1: 88 percent / n-BuLi / tetrahydrofuran / 0.25 h / -70 °C

3.1: 41 percent / diethyl ether; tetrahydrofuran / 1 h / 0 °C

4.1: 52 percent / Na₂HPO₄; sodium amalgam / methanol / 2 h / 20 °C

With disodium hydrogenphosphate; sodium amalgam; n-butyllithium; lithium carbonate; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(02)00038-7

upstream raw materials:

(5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a-homo-26,27-di-n-propyl-9,10-secocholesta-5,7,10⁽¹⁹⁾,24-tetraen-23,25-diol

tert-butyldimethylsilyl chloride

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

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

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