(2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine

Base Information

• Chemical Name: (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine
• CAS No.: 187531-99-3
• Molecular Formula: C₂₀H₂₃NO₂S
• Molecular Weight: 341.474
• Mol file: 187531-99-3.mol

Synonyms:(2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine

Chemical Property of (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine

There total 17 articles about (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine 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: 70.0%

(3S,4S)-5-phenyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1-penten-3-ol → (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine (187531-99-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1021/jo961760o

Reference yield: 48.0%

Carbonic acid methyl ester (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester (220306-82-1) → (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine (187531-99-3) + (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine (187532-00-9)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 65 ℃; for 0.0833333h;

DOI:10.1039/a806882h

Reference yield:

N-((S)-1-Formyl-2-phenyl-ethyl)-2,4,6-trimethyl-benzenesulfonamide (220324-31-2) → (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine (187531-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1: CHCl₃ / 1 h / 0 - 20 °C

2: 86 percent / DIBAL / toluene; CHCl₃ / 1 h / -78 °C

3: 79 percent / Et₃N / tetrahydrofuran / 0.5 h / 0 °C

4: NaH / dimethylformamide / 0.5 h / 0 °C

With sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1039/a806882h

upstream raw materials:

(2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine

Carbonic acid methyl ester (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester

Methanesulfonic acid (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester

2-mesitylenesulphonyl chloride

Downstream raw materials:

tert-butyl (4R,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate