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

Base Information

• Chemical Name: (-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane
• CAS No.: 117406-97-0
• Molecular Formula: C₂₄H₃₄O₃SSi
• Molecular Weight: 430.684
• Mol file: 117406-97-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane 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: 35.0%

(R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-chloro-2-methyl-4-phenyl-3-((R)-toluene-4-sulfinyl)-butan-2-ol (117326-72-4,117406-96-9) → (-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane (117406-97-0) + (-)-(2R,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane (117326-73-5)

Guidance literature:

With potassium hydroxide; In methanol; water; for 0.416667h; Ambient temperature;

DOI:10.1021/jo00274a032

Reference yield:

(-)-menthyl p-toluenesulfinate (1517-82-4) → (-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane (117406-97-0)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jo00274a032

Reference yield:

phenethylmagnesium bromide (3277-89-2) → (-)-(2S,3R)-2,3-epoxy-1-(tert-butyldimethylsiloxy)-2-methyl-4-phenyl-3-(p-tolylsulfinyl)butane (117406-97-0)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jo00274a032

upstream raw materials:

(R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-chloro-2-methyl-4-phenyl-3-((R)-toluene-4-sulfinyl)-butan-2-ol

phenethylmagnesium bromide

(R)-methyl p-tolyl sulfoxide

(R)-chloromethyl p-tolyl sulfoxide

Downstream raw materials:

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

[(2S,3R)-3-Benzyl-3-(tert-butyl-dimethyl-silanyl)-2-methyl-oxiranyl]-methanol

(R)-4-Hydroxy-3-methyl-1-phenyl-3-piperidin-1-yl-butan-2-one