(Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide

Base Information

• Chemical Name: (Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide
• CAS No.: 651358-94-0
• Molecular Formula: C₂₃H₃₂O₂SSi
• Molecular Weight: 400.657
• Mol file: 651358-94-0.mol

Synonyms:(Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide

Chemical Property of (Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide

There total 1 articles about (Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide 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: 90.0%

1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol (95482-80-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide (651358-94-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2003.10.032

Reference yield: 80.0%

(Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide (651358-94-0) → 2-bromo-3-tert-butyldimethylsilyloxy-(4Ss)-(4-methylphenylsulfinyl)-1-phenyl-(1R,2R,3S)-butan-1-ol (651358-95-1)

Guidance literature:

With N-Bromosuccinimide; water; In toluene; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2003.10.032

Reference yield:

(Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide (651358-94-0) → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 80 percent / N-bromosuccinimide; water / toluene / 1 h / 20 °C

2.1: 85 percent / triethylamine / CH₂Cl₂ / 8 h / 20 °C

3.1: 70 percent / NaHMDS / tetrahydrofuran / 1 h / 0 °C

4.1: trifluoroacetic anhydride; triethylamine / acetonitrile / 0.25 h / 0 °C

4.2: 70 percent / NaHCO₃; water / acetonitrile / 0.5 h

5.1: n-butyl lithium / tetrahydrofuran; hexane / 2 h / -23 °C

5.2: 70 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C

6.1: 80 percent / iodosobenzene bis(trifluoroacetate) / acetonitrile; H₂O / 1 h / 0 °C

7.1: 90 percent / triethylamine; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

8.1: Na-Hg; methanol

9.1: 90 percent / hydrogen / Pd(OH)2/C / ethanol / 1 h / 20 °C

10.1: 85 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 20 °C

With methanol; dmap; N-Bromosuccinimide; n-butyllithium; sodium amalgam; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; triethylamine; trifluoroacetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 4.1: Pummerer reaction;

DOI:10.1016/j.tet.2003.10.032

upstream raw materials:

1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

2-bromo-3-tert-butyldimethylsilyloxy-(4Ss)-(4-methylphenylsulfinyl)-1-phenyl-(1R,2R,3S)-butan-1-ol

(+)-preussin

2-bromo-(S_S)-4-(4-methylphenylsulfinyl)-1-phenyl-(2R,2R,3S)-butane-1,3-diol

5-bromo-2,2-dimethyl-(S_S)-4-(4-methylphenylsulfinylmethyl)-6-phenyl-(4S,5R,6R)-1,3-dioxane