dimethyl (S_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate

Base Information

• Chemical Name: dimethyl (S_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate
• CAS No.: 406502-78-1
• Molecular Formula: C₁₇H₂₀NO₄PS
• Molecular Weight: 365.39
• Mol file: 406502-78-1.mol

Synonyms:dimethyl (S_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate

Chemical Property of dimethyl (S_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (S_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate

There total 1 articles about dimethyl (S_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate 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:

(S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → dimethyl (SS,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate (406502-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / n-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

2: 85 percent / n-BuLi / tetrahydrofuran; cyclohexane / -78 - 20 °C

With n-butyllithium; In tetrahydrofuran; cyclohexane;

DOI:10.1021/ol017289p

Reference yield: 84.0%

dimethyl (SS,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate (406502-78-1) → dimethyl (2S,3R)-(-)-3-phenylaziridine-2-phosphonate (406502-80-5)

Guidance literature:

In methanol; diethyl ether; at 20 ℃; for 16h; UV-irradiation; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.05.114

Reference yield:

dimethyl (SS,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate (406502-78-1) → dimethyl (S)-(+)-1-amino-2-phenylethylphosphonate

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / MeMgBr / tetrahydrofuran; diethyl ether / -78 °C

2: 98 percent / HCO₂NH₄ / 10 percent Pd/C / methanol / 16 h

With methylmagnesium bromide; ammonium formate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/jo020707z

upstream raw materials:

(S,E)-N-benzylidene-4-methylbenzenesulfinamide

Downstream raw materials:

dimethyl (2S,3R)-(-)-3-phenylaziridine-2-phosphonate

dimethyl (2R)-(+)-2-phenyl-2H-azirine 3-phosphonate