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

Base Information

• Chemical Name: (1S,2R,3S,S_S)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide
• CAS No.: 1418016-87-1
• Molecular Formula: C₁₉H₂₂NO₄PS
• Molecular Weight: 391.428

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about (1S,2R,3S,S_S)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide 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: 79.0%

(1R,2S,3S)-dimethoxyphosphoryl-2-formyl-3-phenylcyclopropane (1418016-86-0) + (S)-p-toluenesulfinimide (188447-91-8) → (1S,2R,3S,SS)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide (1418016-87-1)

Guidance literature:

With titanium(IV) tetraethanolate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2012.10.085

Reference yield:

(1R,2S,3S)-1-dimethoxyphosphoryl-2-carbomethoxy-3-phenylcyclopropane (459216-72-9) → (1S,2R,3S,SS)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide (1418016-87-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

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

With pyridine; chromium(VI) oxide; titanium(IV) tetraethanolate; lithium borohydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2012.10.085

Reference yield:

(1R,2S,3S)-1-dimethoxyphosphoryl-2-hydroxymethyl-3-phenylcyclopropane (1418016-85-9) → (1S,2R,3S,SS)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide (1418016-87-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; chromium(VI) oxide; titanium(IV) tetraethanolate; In dichloromethane;

DOI:10.1016/j.tet.2012.10.085

upstream raw materials:

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

(S)-p-toluenesulfinimide

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

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

Downstream raw materials:

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

C₂₀H₂₃N₂O₄PS

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