2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan

Base Information

• Chemical Name: 2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan
• CAS No.: 114694-34-7
• Molecular Formula: C₄₄H₇₈O₄Si₂
• Molecular Weight: 727.272
• Mol file: 114694-34-7.mol

Synonyms:2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan

Chemical Property of 2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan

There total 23 articles about 2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan 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:

hydroxybisnorcholenic acid (566-77-8) → 2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan (114694-34-7)

Guidance literature:

Multi-step reaction with 14 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: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) dichloromethane, -60 deg C, 30 min

13: 1.) LDA, 1,10-phenanthroline / 1.) THF, hexane, -75 deg C, 30 min, 2.) 1.5 h

14: 1.) Na₂HPO₄, 2.) 5percent sodium amalgam / 1.) methanol, THF, RT, 30 min, 2.) 5 deg C, 3 h

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

DOI:10.1021/jo00250a009

Reference yield:

3β-hydroxy-22,23-dinor-5,7-choladienic acid methyl ester (99518-39-5) → 2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan (114694-34-7)

Guidance literature:

Multi-step reaction with 11 steps

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

2: pyridine / 20 h / 4 °C

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

4: 12.5 mg / 3.0 M tert-butyl hydroperoxide in toluene, selenium dioxide, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 6 mg / 0.25 h / 55 °C

6: 96 percent / 0.1 N methanolic KOH / diethyl ether / 1.5 h / Ambient temperature

7: 98 percent / imidazole / dimethylformamide / 0.25 h / 55 °C

8: 91 percent / lithium aluminum hydride / tetrahydrofuran / 0.25 h / 0 °C

9: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) dichloromethane, -60 deg C, 30 min

10: 1.) LDA, 1,10-phenanthroline / 1.) THF, hexane, -75 deg C, 30 min, 2.) 1.5 h

11: 1.) Na₂HPO₄, 2.) 5percent sodium amalgam / 1.) methanol, THF, RT, 30 min, 2.) 5 deg C, 3 h

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; selenium(IV) oxide; 1,10-Phenanthroline; oxalyl dichloride; potassium hydrogencarbonate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

Reference yield:

methyl 3β-hydroxy-23-bisnorchol-5-en-22-oate (10527-79-4) → 2-((E)-(2R,5R)-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}-1,1,2-trimethyl-hex-3-enyloxy)-tetrahydro-furan (114694-34-7)

Guidance literature:

Multi-step reaction with 13 steps

1: imidazole / dimethylformamide

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

4: pyridine / 20 h / 4 °C

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

6: 12.5 mg / 3.0 M tert-butyl hydroperoxide in toluene, selenium dioxide, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 6 mg / 0.25 h / 55 °C

8: 96 percent / 0.1 N methanolic KOH / diethyl ether / 1.5 h / Ambient temperature

9: 98 percent / imidazole / dimethylformamide / 0.25 h / 55 °C

10: 91 percent / lithium aluminum hydride / tetrahydrofuran / 0.25 h / 0 °C

11: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) dichloromethane, -60 deg C, 30 min

12: 1.) LDA, 1,10-phenanthroline / 1.) THF, hexane, -75 deg C, 30 min, 2.) 1.5 h

13: 1.) Na₂HPO₄, 2.) 5percent sodium amalgam / 1.) methanol, THF, RT, 30 min, 2.) 5 deg C, 3 h

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; selenium(IV) oxide; 1,10-Phenanthroline; oxalyl dichloride; potassium hydrogencarbonate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

upstream raw materials:

(S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal

2-((R)-3-Benzenesulfonyl-1,1,2-trimethyl-propoxy)-tetrahydro-furan

(2S,5S)-4-Benzenesulfonyl-2-{(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}-5,6-dimethyl-6-(tetrahydro-furan-2-yloxy)-heptan-3-ol

hydroxybisnorcholenic acid

Downstream raw materials:

(24R)-1α,25-dihydroxyvitamin D₂

(E)-(3R,6R)-6-{(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}-2,3-dimethyl-hept-4-en-2-ol