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

Base Information

• Chemical Name: tert-butyl (4R,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate
• CAS No.: 189291-26-7
• Molecular Formula: C₂₅H₃₁NO₄S
• Molecular Weight: 441.591
• Mol file: 189291-26-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about tert-butyl (4R,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate 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: 78.0%

tert-butyl (4S,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate (189291-28-9) → tert-butyl (4R,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate (189291-26-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 15 ℃; for 31h;

DOI:10.1021/jo962094u

Reference yield:

(tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5) → tert-butyl (4R,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate (189291-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Zn / 1) AcOEt, -78 deg C; 2) AcOEt, -78 --> 0 deg C, 30 min; 3) AcOEt, 0 deg C, 1 h

2: 78 percent / Pd(PPh₃)4 / tetrahydrofuran / 31 h / 15 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ozone; zinc; In tetrahydrofuran;

DOI:10.1021/jo962094u

Reference yield:

(2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine (187532-00-9) → tert-butyl (4R,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate (189291-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Zn / 1) AcOEt, -78 deg C; 2) AcOEt, -78 --> 0 deg C, 30 min; 3) AcOEt, 0 deg C, 1 h

2: 78 percent / Pd(PPh₃)4 / tetrahydrofuran / 31 h / 15 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ozone; zinc; In tetrahydrofuran;

DOI:10.1021/jo962094u

upstream raw materials:

(tert-Butoxycarbonylmethylene)triphenylphosphorane

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

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

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