(S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate

Base Information

• Chemical Name: (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate
• CAS No.: 713526-04-6
• Molecular Formula: C₂₄H₃₄NO₆PS
• Molecular Weight: 495.577

Synonyms:(S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate

Chemical Property of (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate

Chemical Property:

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Technology Process of (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate

There total 1 articles about (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate 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: 87.0%

Diethyl phosphonate (762-04-9,123-22-8) + (S)-(+)-N-[5,5-(ethylenedioxy)-5-phenyl-pentanylidene]-p-toluenesulfinamide (332072-74-9) → (SS,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate (713526-04-6) + (SS,S)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate

Guidance literature:

Diethyl phosphonate; With lithium hexamethyldisilazane; In tetrahydrofuran; for 0.25h;

(S)-(+)-N-[5,5-(ethylenedioxy)-5-phenyl-pentanylidene]-p-toluenesulfinamide; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo040127x

Reference yield: 80.0%

(SS,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate (713526-04-6) → (R)-(-)-O,O-diethyl 6-phenyl-2,3,4,5-tetrahydropyridine-2-phosphonate (713526-08-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo040127x

Reference yield:

(SS,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-5,5-(ethylenedioxy)-5-phenylpentylphosphonate (713526-04-6) → (2R,6R)-(-)-O,O-diethyl 6-methylpiperidine-2-phosphonate

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / aq. HCl / tetrahydrofuran / 0 °C

2: 87 percent / H₂ / PtO₂ / ethanol / 20 °C

With hydrogenchloride; hydrogen; platinum(IV) oxide; In tetrahydrofuran; ethanol;

DOI:10.1021/jo040127x

upstream raw materials:

Diethyl phosphonate

(S)-(+)-N-[5,5-(ethylenedioxy)-5-phenyl-pentanylidene]-p-toluenesulfinamide

Downstream raw materials:

(R)-(-)-O,O-diethyl 6-phenyl-2,3,4,5-tetrahydropyridine-2-phosphonate

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