(4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole

Base Information

• Chemical Name: (4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole
• CAS No.: 262592-90-5
• Molecular Formula: C₁₆H₂₂BrNO₂Si
• Molecular Weight: 368.346
• Mol file: 262592-90-5.mol

Synonyms:(4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole

Chemical Property of (4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole

There total 1 articles about (4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole 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: 89.0%

chloro-trimethyl-silane (75-77-4) + (4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole (173531-24-3) → (4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole (262592-90-5)

Guidance literature:

With lithium bromide; In acetonitrile; at 5 - 10 ℃; for 3h;

DOI:10.1016/S0040-4020(99)01018-2

Reference yield: 71.0%

2-dodecenyl phenyl sulfone (104683-16-1) + (4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole (262592-90-5) → (4S,1'R,2'E,5'RS,6'E)-2-phenyl-4-(5'-phenylsulfonyl-1'-trimethylsilyloxyhexadeca-2',6'-dienyl)-4,5-dihydrooxazole (262592-91-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -40 - 10 ℃;

DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

(4S,1'S,2'S)-2-phenyl-4-(2'-bromo-1'-trimethylsilyloxy-3'-butenyl)-4,5-dihydrooxazole (262592-90-5) → (2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol (115018-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 71 percent / n-BuLi / tetrahydrofuran; hexane / -40 - 10 °C

2.1: LiBEt₃H; dppp / Pd(OAc)2 / 1 h / 0 °C

2.2: aq. HCl / tetrahydrofuran / 15 h / 20 °C

2.3: 41 percent / Et₃N / dimethylformamide / 5 h / 60 °C

With n-butyllithium; 1,3-bis-(diphenylphosphino)propane; lithium triethylborohydride; palladium diacetate; In tetrahydrofuran; hexane; 1.1: Substitution / 2.1: desulfonylation / 2.2: Ring cleavage / 2.3: Acylation;

DOI:10.1016/S0040-4020(99)01018-2

upstream raw materials:

chloro-trimethyl-silane

(4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole

Downstream raw materials:

(4S,1'R,2'E,5'RS,6'E)-2-phenyl-4-(5'-phenylsulfonyl-1'-trimethylsilyloxyhexadeca-2',6'-dienyl)-4,5-dihydrooxazole

(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol