(S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate

Base Information

• Chemical Name: (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate
• CAS No.: 713526-02-4
• Molecular Formula: C₂₀H₃₄NO₆PS
• Molecular Weight: 447.533

Synonyms:(S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate

Chemical Property of (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate

Chemical Property:

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Technology Process of (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate

There total 3 articles about (S_S,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate 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: 91.0%

Diethyl phosphonate (762-04-9,123-22-8) + (S)-(+)-N-[6,6-(ethylenedioxy)heptanylidene]-p-toluenesulfinamide (713525-95-2) → (SS,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate (713526-02-4) + (SS,S)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate

Guidance literature:

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

(S)-(+)-N-[6,6-(ethylenedioxy)heptanylidene]-p-toluenesulfinamide; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo040127x

Reference yield:

methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate (145068-76-4) → (SS,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate (713526-02-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

2.1: 62 percent / Ti(OEt)4 / CH₂Cl₂ / 20 °C

3.1: LiHMDS / tetrahydrofuran / 0.25 h

3.2: 91 percent / tetrahydrofuran / -78 °C

With titanium(IV) tetraethanolate; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo040127x

Reference yield:

2-Methyl-2-(5-oxopentyl)-1,3-dioxolane (142055-97-8) → (SS,R)-(+)-O,O-diethyl N-(p-toluenesulfinyl)-1-amino-6,6-(ethylenedioxy)hexylphosphonate (713526-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 62 percent / Ti(OEt)4 / CH₂Cl₂ / 20 °C

2.1: LiHMDS / tetrahydrofuran / 0.25 h

2.2: 91 percent / tetrahydrofuran / -78 °C

With titanium(IV) tetraethanolate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo040127x

upstream raw materials:

Diethyl phosphonate

(S)-(+)-N-[6,6-(ethylenedioxy)heptanylidene]-p-toluenesulfinamide

methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

2-Methyl-2-(5-oxopentyl)-1,3-dioxolane

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