(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene

Base Information

• Chemical Name: (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene
• CAS No.: 142777-80-8
• Molecular Formula: C₄₈H₉₂O₃Si₃
• Molecular Weight: 801.513
• Mol file: 142777-80-8.mol

Synonyms:

Chemical Property of (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene

There total 13 articles about (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-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:

Acetic acid 2-benzenesulfonyl-1-((S)-1-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-ethyl)-6-ethyl-6-triethylsilanyloxy-octyl ester → (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene (142777-80-8)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)79565-7

Reference yield:

5-Chlorovaleroyl chloride (1575-61-7) → (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene (142777-80-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature

2: 92 percent / t-BuOK / dimethylformamide / 16 h / Ambient temperature

3: 67 percent / 3-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 2 h / Ambient temperature

4: 99 percent / TEA / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 1) LDA / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 1 h

6: pyridine, DMAP / 16 h / 4 °C

7: 5percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; TEA; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79565-7

Reference yield:

1-chloro-5-ethylheptan-5-ol (31848-92-7) → (1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene (142777-80-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / t-BuOK / dimethylformamide / 16 h / Ambient temperature

2: 67 percent / 3-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 2 h / Ambient temperature

3: 99 percent / TEA / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 1) LDA / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 1 h

5: pyridine, DMAP / 16 h / 4 °C

6: 5percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; TEA; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79565-7

upstream raw materials:

5-Chlorovaleroyl chloride

1-chloro-5-ethylheptan-5-ol

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

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

Downstream raw materials:

Δ²²,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3