(2S,1'S,2'R,3'S,S_S)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile

Base Information

• Chemical Name: (2S,1'S,2'R,3'S,S_S)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile
• CAS No.: 1418016-88-2
• Molecular Formula: C₂₀H₂₃N₂O₄PS
• Molecular Weight: 418.453

Synonyms:(2S,1'S,2'R,3'S,S_S)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile

Chemical Property of (2S,1'S,2'R,3'S,S_S)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile

Chemical Property:

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Technology Process of (2S,1'S,2'R,3'S,S_S)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile

There total 5 articles about (2S,1'S,2'R,3'S,S_S)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile 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%

(1S,2R,3S,SS)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide (1418016-87-1) + diethylaluminium cyanide (5804-85-3) → (2S,1'S,2'R,3'S,SS)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile (1418016-88-2) + C20H23N2O4PS (1418016-95-1)

Guidance literature:

diethylaluminium cyanide; With isopropyl alcohol; In tetrahydrofuran; at -78 - 20 ℃; for 0.5h;

(1S,2R,3S,S_S)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide; In tetrahydrofuran; at -78 - 20 ℃; for 24h; Overall yield = 83 %; diastereoselective reaction;

DOI:10.1016/j.tet.2012.10.085

Reference yield:

1-dimethoxyphosphoryl-1-p-tolylsulfinyl-2-carbomethoxy-3-phenylcyclopropane → (2S,1'S,2'R,3'S,SS)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile (1418016-88-2) + C20H23N2O4PS (1418016-95-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: disodium hydrogenphosphate; sodium amalgam / methanol / 1 h / -20 °C

1.2: -20 - 0 °C

2.1: lithium borohydride / tetrahydrofuran; methanol / 24 h / 20 °C

3.1: chromium(VI) oxide; pyridine / dichloromethane / 12 h / 20 °C

4.1: titanium(IV) tetraethanolate / dichloromethane / 24 h / 20 °C

5.1: isopropyl alcohol / tetrahydrofuran / 0.5 h / -78 - 20 °C

5.2: 24 h / -78 - 20 °C

With pyridine; chromium(VI) oxide; titanium(IV) tetraethanolate; disodium hydrogenphosphate; lithium borohydride; sodium amalgam; isopropyl alcohol; In tetrahydrofuran; methanol; dichloromethane; 5.1: |Strecker Aminoacid Synthesis / 5.2: |Strecker Aminoacid Synthesis;

DOI:10.1016/j.tet.2012.10.085

Reference yield:

(1R,2S,3S)-1-dimethoxyphosphoryl-2-carbomethoxy-3-phenylcyclopropane (459216-72-9) → (2S,1'S,2'R,3'S,SS)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile (1418016-88-2) + C20H23N2O4PS (1418016-95-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium borohydride / tetrahydrofuran; methanol / 24 h / 20 °C

2.1: chromium(VI) oxide; pyridine / dichloromethane / 12 h / 20 °C

3.1: titanium(IV) tetraethanolate / dichloromethane / 24 h / 20 °C

4.1: isopropyl alcohol / tetrahydrofuran / 0.5 h / -78 - 20 °C

4.2: 24 h / -78 - 20 °C

With pyridine; chromium(VI) oxide; titanium(IV) tetraethanolate; lithium borohydride; isopropyl alcohol; In tetrahydrofuran; methanol; dichloromethane; 4.1: |Strecker Aminoacid Synthesis / 4.2: |Strecker Aminoacid Synthesis;

DOI:10.1016/j.tet.2012.10.085

upstream raw materials:

(1S,2R,3S,S_S)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide

diethylaluminium cyanide

(1R,2S,3S)-1-dimethoxyphosphoryl-2-carbomethoxy-3-phenylcyclopropane

(1R,2S,3S)-1-dimethoxyphosphoryl-2-hydroxymethyl-3-phenylcyclopropane

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