(1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

Base Information

• Chemical Name: (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol
• CAS No.: 386766-81-0
• Molecular Formula: C₄₂H₅₈O₃Si
• Molecular Weight: 639.006

Synonyms:

Chemical Property of (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

There total 12 articles about (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-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:

1-[(1R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aR,7aR)-1-[(R)-5-(2-ethoxy-ethoxy)-1,5-dimethyl-hex-3-ynyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol → (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol (386766-81-0) + (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4Z)-ylidene]-eth-(E)-ylidene]-cyclohexanol + (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-cyclohexanol

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; water; at 40 - 60 ℃; for 4h;

DOI:10.1002/1099-0690(200110)2001:20<3779::AID-EJOC3779>3.0.CO;2-Q

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol (386766-81-0)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 20 °C

2: K₂CO₃ / methanol / 20 °C

3: Et₃N; DMAP / 20 °C

4: 81 percent / tBuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 55 - 60 °C

5: DIBAL-H / CH₂Cl₂ / -78 - -55 °C

6: PCC / CH₂Cl₂ / 1 h / 20 °C

7: t-BuLi / tetrahydrofuran; pentane / 1 h / -70 °C

8: PTSA / dioxane; H₂O / 4 h / 40 - 60 °C

With 1H-imidazole; dmap; potassium tert-butylate; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;

DOI:10.1002/1099-0690(200110)2001:20<3779::AID-EJOC3779>3.0.CO;2-Q

Reference yield:

(1S,3S,5R)-3-acetoxy-5-hydroxy-1-(methoxycarbonyl)cyclohexane (326598-94-1) → (1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol (386766-81-0)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 20 °C

2: K₂CO₃ / methanol / 20 °C

3: Et₃N; DMAP / 20 °C

4: 81 percent / tBuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 55 - 60 °C

5: DIBAL-H / CH₂Cl₂ / -78 - -55 °C

6: PCC / CH₂Cl₂ / 1 h / 20 °C

7: t-BuLi / tetrahydrofuran; pentane / 1 h / -70 °C

8: PTSA / dioxane; H₂O / 4 h / 40 - 60 °C

With 1H-imidazole; dmap; potassium tert-butylate; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;

DOI:10.1002/1099-0690(200110)2001:20<3779::AID-EJOC3779>3.0.CO;2-Q

upstream raw materials:

tert-butylchlorodiphenylsilane

(1S,3S,5R)-3-acetoxy-5-hydroxy-1-(methoxycarbonyl)cyclohexane

(2S,3aR,4aR)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]hexane-3a-carbaldehyde

[(1R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-yl]-methanol

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