dimethyl (S_S,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate

Base Information

• Chemical Name: dimethyl (S_S,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate
• CAS No.: 406502-76-9
• Molecular Formula: C₁₇H₂₁ClNO₄PS
• Molecular Weight: 401.851

Synonyms:dimethyl (S_S,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate

Chemical Property of dimethyl (S_S,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate

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Technology Process of dimethyl (S_S,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate

There total 2 articles about dimethyl (S_S,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate 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: 58.0%

dimethyl α-chloromethylphosphonate (6346-15-2) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → dimethyl (SS,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate (406502-76-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h;

DOI:10.1021/ol017289p

Reference yield: 58.0%

dimethyl α-chloromethylphosphonate (6346-15-2) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → dimethyl (SS,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate (406502-76-9) + dimethyl (Ss,2S)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate + dimethyl (Ss,1R,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h;

DOI:10.1021/jo020707z

Reference yield:

dimethyl (SS,1S,2R)-(+)-1-chloro-2-phenyl-2-(p-toluenesulfinamide)-ethylphosphonate (406502-76-9) → dimethyl (S)-(+)-1-amino-2-phenylethylphosphonate

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / n-BuLi / tetrahydrofuran; cyclohexane / 1 h / -78 - 20 °C

2: 70 percent / MeMgBr / tetrahydrofuran; diethyl ether / -78 °C

3: 98 percent / HCO₂NH₄ / 10 percent Pd/C / methanol / 16 h

With n-butyllithium; methylmagnesium bromide; ammonium formate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; cyclohexane;

DOI:10.1021/jo020707z

upstream raw materials:

dimethyl α-chloromethylphosphonate

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

Downstream raw materials:

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

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

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