diethyl (S_s,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate

Base Information

• Chemical Name: diethyl (S_s,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate
• CAS No.: 220586-50-5
• Molecular Formula: C₁₉H₂₅ClNO₄PS
• Molecular Weight: 429.905
• Mol file: 220586-50-5.mol

Synonyms:diethyl (S_s,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate

Chemical Property of diethyl (S_s,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (S_s,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate

There total 1 articles about diethyl (S_s,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)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%

diethyl chloromethylphosphonate (3167-63-3) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → diethyl (Ss,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate (220586-50-5) + diethyl (Ss,1R,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate (220586-51-6)

Guidance literature:

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

DOI:10.1016/S0040-4039(98)02331-4

Reference yield: 76.0%

diethyl (Ss,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate (220586-50-5) → diethyl (Ss,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate (220586-52-7)

Guidance literature:

With sodium hydride;

DOI:10.1016/S0040-4039(98)02331-4

Reference yield:

diethyl (Ss,1S,2R)-1-chloro-2-phenyl-2-(p-toluenesulfinamido)ethylphosphonate (220586-50-5) → (S)-(1-Amino-2-phenylethyl)phosphonsaeure-diethylester (68839-08-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / NaH / tetrahydrofuran; cyclohexane / 1 h / -78 - 20 °C

2: 84 percent / TFA / acetone; H₂O / 1 h / 20 °C

3: 99 percent / HCO₂NH₄ / 10 percent Pd/C / methanol / 16 h

With ammonium formate; sodium hydride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; cyclohexane; water; acetone;

DOI:10.1021/jo020707z

upstream raw materials:

diethyl chloromethylphosphonate

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

Downstream raw materials:

diethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate

(S)-(1-Amino-2-phenylethyl)phosphonsaeure-diethylester

diethyl(-)-(2S,3R)-(3-phenyl-2-H-aziridin-2-yl) phosphonate

diethyl(-)-S-(3-phenyl-2-H-azirin-2-yl) phosphonate