(1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol

Base Information

• Chemical Name: (1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol
• CAS No.: 83198-15-6
• Molecular Formula: C₂₈H₄₄O
• Molecular Weight: 396.657
• Mol file: 83198-15-6.mol

Synonyms:(1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol

Chemical Property of (1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol

There total 11 articles about (1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol 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:

2,5-dimethyl-1,3-cyclohexanedione (61621-47-4) → (1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol (83198-15-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 66 percent / iodine, triphenylphosphine, triethylamine / acetonitrile / 14 h / Heating

2: 67 percent / sodium borohydride / ethanol / 0.33 h

3: imidazole

4: 1.) tert-butyllithium, 2.) CuI, (n-Bu)3P, 3.) (n-Bu)4NF

5: 32 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 0.5 h

6: 69 percent / KOH, MeOH / tetrahydrofuran / 21 h / Ambient temperature

7: 2,2,4-trimethyl-pentane / 11 h / 100 °C

With 1H-imidazole; methanol; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; tributylphosphine; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 2,2,4-trimethylpentane; ethanol; acetonitrile; benzene;

DOI:10.1021/ja00386a042

Reference yield:

de-A,B-25-cholesten-8β-ol (66774-82-1) → (1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol (83198-15-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / pyridinium dichromate, pyridinium trifluoroacetate / CH₂Cl₂ / 4.5 h

2: 93 percent / n-butyllithium / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) room temperature, 1 h

3: 70 percent / n-butyllithium / tetrahydrofuran / 1.) -78 deg C, 2.) room temperature, 3 h

4: 1.) tert-butyllithium, 2.) CuI, (n-Bu)3P, 3.) (n-Bu)4NF

5: 32 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 0.5 h

6: 69 percent / KOH, MeOH / tetrahydrofuran / 21 h / Ambient temperature

7: 2,2,4-trimethyl-pentane / 11 h / 100 °C

With methanol; potassium hydroxide; copper(l) iodide; dipyridinium dichromate; n-butyllithium; tributylphosphine; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium trifluroacetate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; benzene;

DOI:10.1021/ja00386a042

Reference yield:

de-A,B-25-cholesten-8-one (83076-51-1) → (1S,2R,5R)-3-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hex-5-enyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-(4Z)-ylidene]-eth-(Z)-ylidene]-2,5-dimethyl-cyclohexanol (83198-15-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / n-butyllithium / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) room temperature, 1 h

2: 70 percent / n-butyllithium / tetrahydrofuran / 1.) -78 deg C, 2.) room temperature, 3 h

3: 1.) tert-butyllithium, 2.) CuI, (n-Bu)3P, 3.) (n-Bu)4NF

4: 32 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 0.5 h

5: 69 percent / KOH, MeOH / tetrahydrofuran / 21 h / Ambient temperature

6: 2,2,4-trimethyl-pentane / 11 h / 100 °C

With methanol; potassium hydroxide; copper(l) iodide; n-butyllithium; tributylphosphine; tetrabutyl ammonium fluoride; tert.-butyl lithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 2,2,4-trimethylpentane; benzene;

DOI:10.1021/ja00386a042

upstream raw materials:

(1S,3R,6R)-1-hydroxy-3-methyl-9,10-seco-cholesta-5⁽¹⁰⁾,6,7,25-tetraene

2,5-dimethyl-1,3-cyclohexanedione

de-A,B-25-cholesten-8β-ol

de-A,B-25-cholesten-8-one