(S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol

Base Information

• Chemical Name: (S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol
• CAS No.: 142777-79-5
• Molecular Formula: C₅₄H₉₈O₆SSi₃
• Molecular Weight: 959.691

Synonyms:

Chemical Property of (S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol

There total 10 articles about (S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol 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:

5-Chlorovaleroyl chloride (1575-61-7) → (S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol (142777-79-5)

Guidance literature:

Multi-step reaction with 5 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

With TEA; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; 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) → (S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol (142777-79-5)

Guidance literature:

Multi-step reaction with 4 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

With TEA; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → (S)-4-Benzenesulfonyl-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-8-ethyl-8-triethylsilanyloxy-decan-3-ol (142777-79-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / pyridine / -20 - 0 °C

2: 88 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 1 h / Ambient temperature

3: n-BuLi / tetrahydrofuran / -78 °C

4: 88 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 25 min, 2) RT, 20 min

5: 1) (COCl)2, 2) Et₃N / 1) DMSO, CH₂Cl₂, -60 deg C, 30 min.

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

With pyridine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

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

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

(5-Benzenesulfonyl-1,1-diethyl-pentyloxy)-triethyl-silane

5-Chlorovaleroyl chloride

1-chloro-5-ethylheptan-5-ol

Downstream raw materials:

(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

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

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