4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene

Base Information

• Chemical Name: 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene
• CAS No.: 827032-51-9
• Molecular Formula: C₅₇H₁₁₆O₅Si₅
• Molecular Weight: 1021.97

Synonyms:4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene

Chemical Property of 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene

There total 14 articles about 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-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:

(1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane (139356-39-1) + (1R,3aR,7aR)-1-[(1R,4R)-4-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1-(4-methyl-4-(trimethylsilanyloxy)pentyl)-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-one (792959-65-0) → 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene (827032-51-9)

Guidance literature:

(1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.166667h;

(1R,3aR,7aR)-1-[(1R,4R)-4-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1-(4-methyl-4-(trimethylsilanyloxy)pentyl)-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-one; In tetrahydrofuran; hexane; for 4h;

DOI:10.1021/jm049340b

Reference yield:

(2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate (77522-15-7) → 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene (827032-51-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 0.8586 g / BuLi / tetrahydrofuran; hexane / 6 h / -20 °C

2.1: sodium amalgam; MeOH / tetrahydrofuran / 14 h

2.2: 0.45 g / oxalic acid dihydrate / methanol

3.1: 85 percent / aq. fluorosilic acid / acetonitrile; dioxane / 3.25 h / 20 °C

4.1: pyridinium tosylate / acetone / 12 h / 20 °C

4.2: H₂O / 0.17 h

5.1: 0.3452 g / pyridine / 34 h / 20 - 35 °C

6.1: aq. AcOH / 2.5 h / Heating

7.1: imidazole / dimethylformamide / 48 h / 20 °C

7.2: 4-(N,N-dimethylamino)pyridine / dimethylformamide / 24 h

8.1: 0.3372 g / cyclohexane / 12 h

9.1: LiAlH₄ / tetrahydrofuran / 1.5 h

10.1: 0.2988 g / pyridinium dichromate; Celite / CH₂Cl₂ / 4.5 h

11.1: BuLi / hexane; tetrahydrofuran / 0.17 h / -70 °C

11.2: hexane; tetrahydrofuran / 4 h

With pyridine; 1H-imidazole; methanol; sodium amalgam; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; Celite; fluorosilic acid; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; acetonitrile; 11.2: Wittig-Horner reaction;

DOI:10.1021/jm049340b

Reference yield:

(S)-6-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-7-iodo-2-methyl-heptan-2-ol → 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene (827032-51-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / dimethylformamide / 18 h / 20 - 40 °C

2.1: 87 percent / cyclohexane

3.1: 0.8586 g / BuLi / tetrahydrofuran; hexane / 6 h / -20 °C

4.1: sodium amalgam; MeOH / tetrahydrofuran / 14 h

4.2: 0.45 g / oxalic acid dihydrate / methanol

5.1: 85 percent / aq. fluorosilic acid / acetonitrile; dioxane / 3.25 h / 20 °C

6.1: pyridinium tosylate / acetone / 12 h / 20 °C

6.2: H₂O / 0.17 h

7.1: 0.3452 g / pyridine / 34 h / 20 - 35 °C

8.1: aq. AcOH / 2.5 h / Heating

9.1: imidazole / dimethylformamide / 48 h / 20 °C

9.2: 4-(N,N-dimethylamino)pyridine / dimethylformamide / 24 h

10.1: 0.3372 g / cyclohexane / 12 h

11.1: LiAlH₄ / tetrahydrofuran / 1.5 h

12.1: 0.2988 g / pyridinium dichromate; Celite / CH₂Cl₂ / 4.5 h

13.1: BuLi / hexane; tetrahydrofuran / 0.17 h / -70 °C

13.2: hexane; tetrahydrofuran / 4 h

With pyridine; 1H-imidazole; methanol; sodium amalgam; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; Celite; fluorosilic acid; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; acetonitrile; 13.2: Wittig-Horner reaction;

DOI:10.1021/jm049340b

upstream raw materials:

(1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane

(1R,3aR,7aR)-1-[(1R,4R)-4-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1-(4-methyl-4-(trimethylsilanyloxy)pentyl)-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-one

(2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate

(1R,3R,6R)-6-((3aR,4S,7aR)-4-hydroxy-7a-methyloctahydroinden-1-yl)-2,10-dimethylundecane-2,3,10-triol

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