(S_S,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate

Base Information

• Chemical Name: (S_S,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate
• CAS No.: 769195-88-2
• Molecular Formula: C₁₉H₂₄F₂NO₄PS
• Molecular Weight: 431.44

Synonyms:(S_S,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate

Chemical Property of (S_S,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate

Chemical Property:

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Technology Process of (S_S,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate

There total 1 articles about (S_S,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate 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: 74.0%

Diethyl difluoromethylphosphonate (1478-53-1) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → (SS,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate (769195-88-2) + (SS,S)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate

Guidance literature:

Diethyl difluoromethylphosphonate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

(S,E)-N-benzylidene-4-methylbenzenesulfinamide; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/j.tet.2006.08.017

Reference yield: 92.0%

(SS,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate (769195-88-2) → (R)-β-amino-α,α-difluoromethylphosphonate (769195-94-0)

Guidance literature:

With trifluoroacetic acid; In ethanol; at 0 - 20 ℃;

DOI:10.1016/j.tet.2006.08.017

Reference yield:

(SS,R)-diethyl N-(p-toluenesulfinyl)-2-amino-1,1-difluoro-2-phenylethylphosphonate (769195-88-2) → (R)-2-amino-1,1-difluoro-2-phenylethylphosphonic acid (769195-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / trifluoroacetic acid / ethanol / 0 - 20 °C

2.1: HCl / 8 h / Heating

2.2: 84 percent / propylene oxide / ethanol / 3 h

With hydrogenchloride; trifluoroacetic acid; In ethanol;

DOI:10.1016/j.tet.2006.08.017

upstream raw materials:

Diethyl difluoromethylphosphonate

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

Downstream raw materials:

(R)-β-amino-α,α-difluoromethylphosphonate

(R)-monoethyl N-benzyloxycarbonyl-2-amino-1,1-difluoro-2-phenylethylphosphonate

(R)-diethyl N-benzyloxycarbonyl-2-amino-1,1-difluoro-2-phenylethylphosphonate

(R)-2-amino-1,1-difluoro-2-phenylethylphosphonic acid

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