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

Base Information

• Chemical Name: (4S,1'R,2'E,5'RS,6'E)-2-phenyl-4-(5'-phenylsulfonyl-1'-trimethylsilyloxyhexadeca-2',6'-dienyl)-4,5-dihydrooxazole
• CAS No.: 262592-91-6
• Molecular Formula: C₃₄H₄₉NO₄SSi
• Molecular Weight: 595.919

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (4S,1'R,2'E,5'RS,6'E)-2-phenyl-4-(5'-phenylsulfonyl-1'-trimethylsilyloxyhexadeca-2',6'-dienyl)-4,5-dihydrooxazole

There total 4 articles about (4S,1'R,2'E,5'RS,6'E)-2-phenyl-4-(5'-phenylsulfonyl-1'-trimethylsilyloxyhexadeca-2',6'-dienyl)-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: 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:

sodium benzenesulfonate (873-55-2) → (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:

Multi-step reaction with 2 steps

1: 90 percent / dimethylformamide / 5 h / 50 °C

2: 71 percent / n-BuLi / tetrahydrofuran; hexane / -40 - 10 °C

With n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution;

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

Reference yield:

(E)-2-dodecenyl chloride (71518-12-2) → (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:

Multi-step reaction with 2 steps

1: 90 percent / dimethylformamide / 5 h / 50 °C

2: 71 percent / n-BuLi / tetrahydrofuran; hexane / -40 - 10 °C

With n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution;

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

upstream raw materials:

2-dodecenyl phenyl sulfone

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

sodium benzenesulfonate

(E)-2-dodecenyl chloride

Downstream raw materials:

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

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