(1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene

Base Information

• Chemical Name: (1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene
• CAS No.: 114694-26-7
• Molecular Formula: C₅₃H₉₂O₅SSi₃
• Molecular Weight: 925.633
• Mol file: 114694-26-7.mol

Synonyms:

Chemical Property of (1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene

There total 21 articles about (1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene 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:

triethylsilyl chloride (994-30-9) → (1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene (114694-26-7,114694-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 2 h / Ambient temperature

2: 1.) LDA, 1,10-phenanthroline / 1.) a.) THF, hexane, -75 deg C, 30 min, b.) -21 deg C, 15 min, 2.) -20 to -10 deg C, 3.5 h

With 1H-imidazole; 1,10-Phenanthroline; lithium diisopropyl amide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

Reference yield:

1-(2'-hydroxyethyl)-1-cyclopentanol (73089-93-7) → (1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene (114694-26-7,114694-27-8)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 20 h / 4 °C

2: potassium tert-butoxide / dimethylformamide / Ambient temperature; overnight

3: 80-85percent 3-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 2 h

4: imidazole / dimethylformamide / 2 h / Ambient temperature

5: 1.) LDA, 1,10-phenanthroline / 1.) a.) THF, hexane, -75 deg C, 30 min, b.) -21 deg C, 15 min, 2.) -20 to -10 deg C, 3.5 h

With pyridine; 1H-imidazole; 1,10-Phenanthroline; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

Reference yield:

hydroxybisnorcholenic acid (566-77-8) → (1R,3aS,7aR)-1-[(R)-3-Benzenesulfonyl-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene (114694-26-7,114694-27-8)

Guidance literature:

Multi-step reaction with 13 steps

1: H₂SO₄

2: imidazole / dimethylformamide

4: 1.) benzene, ethyl ether, irradiation, 40 min, 2.) ethanol, reflux, 3 h

5: pyridine / 20 h / 4 °C

6: potassium bicarbonate / CH₂Cl₂ / 24 h / 55 °C

7: 12.5 mg / 3.0 M tert-butyl hydroperoxide in toluene, selenium dioxide, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 6 mg / 0.25 h / 55 °C

9: 96 percent / 0.1 N methanolic KOH / diethyl ether / 1.5 h / Ambient temperature

10: 98 percent / imidazole / dimethylformamide / 0.25 h / 55 °C

11: 91 percent / lithium aluminum hydride / tetrahydrofuran / 0.25 h / 0 °C

12: 98 percent / pyridine / 22 h / 5 °C

13: 1.) LDA, 1,10-phenanthroline / 1.) a.) THF, hexane, -75 deg C, 30 min, b.) -21 deg C, 15 min, 2.) -20 to -10 deg C, 3.5 h

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; potassium hydroxide; lithium aluminium tetrahydride; selenium(IV) oxide; 1,10-Phenanthroline; sulfuric acid; potassium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

upstream raw materials:

1-<2-(phenylsulfonyl)ethyl>-1-<(triethylsilyl)oxy>cyclopentane

(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

triethylsilyl chloride

1-(2'-hydroxyethyl)-1-cyclopentanol

Downstream raw materials:

26,27-trimethylene-1,25-dihydroxyvitamin D₃

(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-1-[(R)-1-methyl-4-(1-triethylsilanyloxy-cyclopentyl)-butyl]-octahydro-indene