dimethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate

Base Information

• Chemical Name: dimethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate
• CAS No.: 511544-96-0
• Molecular Formula: C₁₈H₁₉F₃NO₄PS
• Molecular Weight: 433.388

Synonyms:dimethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate

Chemical Property of dimethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate

Chemical Property:

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Technology Process of dimethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate

There total 1 articles about dimethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-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: 78.0%

dimethyl (Ss,1S,2R)-(+)-1-chloro-2-(4-trifluoromethylphenyl)-2-(p-toluenesulfinamido)ethylphosphonate (511544-67-5) → dimethyl (Ss,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate (511544-96-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; for 1h;

DOI:10.1021/jo020707z

Reference yield: 72.0%

dimethyl (Ss,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate (511544-96-0) → dimethyl (2S,3R)-(-)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate (511545-12-3)

Guidance literature:

With methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃;

DOI:10.1021/jo020707z

Reference yield:

dimethyl (Ss,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate (511544-96-0) → dimethyl (S)-(+)-1-amino-2-(p-trifluoromethylphenyl)ethylphosphonate

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / MeMgBr / tetrahydrofuran; diethyl ether / -78 °C

2: 67 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:

dimethyl (S_s,1S,2R)-(+)-1-chloro-2-(4-trifluoromethylphenyl)-2-(p-toluenesulfinamido)ethylphosphonate

Downstream raw materials:

dimethyl (2S,3R)-(-)-3-(p-trifluoromethylphenyl)aziridine-2-phosphonate

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