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

Base Information

• Chemical Name: 2-bromo-3-tert-butyldimethylsilyloxy-(4Ss)-(4-methylphenylsulfinyl)-1-phenyl-(1R,2R,3S)-butan-1-ol
• CAS No.: 651358-95-1
• Molecular Formula: C₂₃H₃₃BrO₃SSi
• Molecular Weight: 497.569
• Mol file: 651358-95-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 2-bromo-3-tert-butyldimethylsilyloxy-(4Ss)-(4-methylphenylsulfinyl)-1-phenyl-(1R,2R,3S)-butan-1-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: 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:

1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol (95482-80-7) → 2-bromo-3-tert-butyldimethylsilyloxy-(4Ss)-(4-methylphenylsulfinyl)-1-phenyl-(1R,2R,3S)-butan-1-ol (651358-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

2: 80 percent / N-bromosuccinimide; water / toluene / 1 h / 20 °C

With 1H-imidazole; N-Bromosuccinimide; water; In dichloromethane; toluene;

DOI:10.1016/j.tet.2003.10.032

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2-bromo-3-tert-butyldimethylsilyloxy-(4Ss)-(4-methylphenylsulfinyl)-1-phenyl-(1R,2R,3S)-butan-1-ol (651358-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

2: 80 percent / N-bromosuccinimide; water / toluene / 1 h / 20 °C

With 1H-imidazole; N-Bromosuccinimide; water; In dichloromethane; toluene;

DOI:10.1016/j.tet.2003.10.032

upstream raw materials:

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

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

4-[2-hydroxy-1-tert-butyldimethylsilyloxy-2-(2-nonyl-1,3-dithian-2-yl)-(1R)-ethyl]-3-methyl-5-phenyl-(4S,5R)-1,3-oxazolan-2-one

1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-methyl-2-oxoundecyl acetate

1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-methyl-(1S)-dodecan-3-one

2-hydroxy-1-tert-butyldimethylsilyloxy-1-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,3-oxazolan-4-yl]-(1R)-dodecan-3-one