(2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene

Base Information

• Chemical Name: (2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene
• CAS No.: 257627-66-0
• Molecular Formula: C₂₁H₄₀O₂Si₃
• Molecular Weight: 408.804
• Mol file: 257627-66-0.mol

Synonyms:(2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene

Chemical Property of (2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene

There total 3 articles about (2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene 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: 99.0%

chloro-trimethyl-silane (75-77-4) + (2S,3RS)-5-(dimethylphenylsilyl)-3,4-dimethyl-(E)-pent-4-ene-2,3-diol (257627-65-9) → (2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene (257627-66-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1021/ol991315q

Reference yield:

E-1-iodo-1-(dimethylphenylsilyl)propene (101150-39-4) → (2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene (257627-66-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TaCl₅; Zn / benzene; 1,2-dimethoxy-ethane / 3 h

1.2: tetrahydrofuran; benzene; 1,2-dimethoxy-ethane / 1 h

1.3: aq. NaOH / tetrahydrofuran; benzene; 1,2-dimethoxy-ethane / 2 h

2.1: 82 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

3.1: 99 percent / imidazole / CH₂Cl₂ / 0.17 h / 0 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; tantalum pentachloride; zinc; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; benzene; 1.1: Metallation / 1.2: Addition / 1.3: Hydrolysis / 2.1: Substitution / 3.1: Substitution;

DOI:10.1021/ol991315q

Reference yield:

(E)-(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-2,3-dimethyl-pent-1-en-3-ol (1026453-73-5) → (2S,3RS)-{[2,3-dimethyl-3,4-bis(trimethylsiloxy)-(E)-pent-1-enyl]-dimethylsilanyl}benzene (257627-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

2: 99 percent / imidazole / CH₂Cl₂ / 0.17 h / 0 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Substitution;

DOI:10.1021/ol991315q

upstream raw materials:

chloro-trimethyl-silane

(2S,3RS)-5-(dimethylphenylsilyl)-3,4-dimethyl-(E)-pent-4-ene-2,3-diol

E-1-iodo-1-(dimethylphenylsilyl)propene

(E)-(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-2,3-dimethyl-pent-1-en-3-ol

Downstream raw materials:

(2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(E)-2-(dimethyl-phenyl-silanyl)-1-methyl-vinyl]-2,4,5-trimethyl-[1,3]dioxolane

(2S,3S,4S,5R)-1-[5-((tert-butyldiphenylsiloxy)methyl)-4-(dimethylphenylsilyl)-2,3,5-trimethyltetrahydrofuran-3-yl]ethanone