methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate

Base Information

• Chemical Name: methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate
• CAS No.: 189291-11-0
• Molecular Formula: C₁₄H₁₉NO₄S
• Molecular Weight: 297.375
• Mol file: 189291-11-0.mol

Synonyms:methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate

Chemical Property of methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate

There total 2 articles about methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate 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: 88.0%

methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate (189291-10-9) → methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate (189291-11-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 6h;

DOI:10.1021/jo962094u

Reference yield:

2-mesitylenesulphonyl chloride (773-64-8) → methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate (189291-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) thionyl chloride, 2.) Et₃N / 1) -78 deg C, --> rt, 18 h; 2) DMF, CHCl₃, 0 deg C, 2 h

2: 88 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 6 h / 0 °C

With thionyl chloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo962094u

Reference yield:

methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate (189291-11-0) → (2R,3S)-3-Methyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridine-2-carbaldehyde

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2h;

DOI:10.1021/jo962094u

upstream raw materials:

methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate

2-mesitylenesulphonyl chloride

Downstream raw materials:

(Z)-3-[(2S,3S)-3-Methyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid methyl ester

(E)-3-[(2S,3S)-3-Methyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid methyl ester