(E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol

Base Information

• Chemical Name: (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol
• CAS No.: 117326-76-8
• Molecular Formula: C₁₇H₂₈O₂Si
• Molecular Weight: 292.494
• Mol file: 117326-76-8.mol

Synonyms:(E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol

Chemical Property of (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol

There total 5 articles about (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-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: 63.0%

(-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane (117406-97-0) → (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol (117326-76-8) + [(2S,3R)-3-Benzyl-3-(tert-butyl-dimethyl-silanyl)-2-methyl-oxiranyl]-methanol (117326-77-9)

Guidance literature:

With n-butyllithium; at -65 - -45 ℃;

DOI:10.1016/0040-4039(88)85228-6

Reference yield:

phenethylmagnesium bromide (3277-89-2) → (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol (117326-76-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / toluene / -60 - -20 °C

2: K₂CO₃, N-chlorosuccinimide (NCS) / CH₂Cl₂ / 43 h / Ambient temperature

3: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 50 min

4: 22 percent / KOH / methanol; H₂O / 0.42 h / Ambient temperature

5: 21 percent / n-BuLi / tetrahydrofuran / -70 - -45 °C

With potassium hydroxide; N-chloro-succinimide; n-butyllithium; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1021/jo00274a032

Reference yield:

(RS)-2-phenylethyl p-tolyl sulfoxide (118271-35-5) → (E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-phenyl-but-3-en-2-ol (117326-76-8)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃, N-chlorosuccinimide (NCS) / CH₂Cl₂ / 43 h / Ambient temperature

2: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 50 min

3: 22 percent / KOH / methanol; H₂O / 0.42 h / Ambient temperature

4: 21 percent / n-BuLi / tetrahydrofuran / -70 - -45 °C

With potassium hydroxide; N-chloro-succinimide; n-butyllithium; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo00274a032

upstream raw materials:

(-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane

phenethylmagnesium bromide

(R_S)-2-phenylethyl p-tolyl sulfoxide

(-)-(R)-1-chloro-2-phenylethyl p-tolyl sulfoxide