(2R,3R,1'S,S_S)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

Base Information

• Chemical Name: (2R,3R,1'S,S_S)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane
• CAS No.: 884382-62-1
• Molecular Formula: C₁₉H₂₈O₃S
• Molecular Weight: 336.496

Synonyms:(2R,3R,1'S,S_S)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

Chemical Property of (2R,3R,1'S,S_S)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R,1'S,S_S)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

There total 3 articles about (2R,3R,1'S,S_S)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane 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: 76.0%

(+)-(5S,SS)-(6E,8E)-7-(p-tolylsulfinyl)dodeca-6,8-dien-5-ol (679813-29-7) → ((2R,3S)-3-Butyl-oxiranyl)-(3-propyl-oxiranyl)-methanone + ((2S,3S)-3-Butyl-oxiranyl)-(3-propyl-oxiranyl)-methanone + (2R,3R,1'S,SS)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane (884382-62-1) + (2R,3R,1'S)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfonyl)oxirane

Guidance literature:

With tert.-butylhydroperoxide; sodium hydride; In tetrahydrofuran; at 0 ℃; for 1.16667h;

DOI:10.1016/j.tet.2005.12.024

Reference yield:

(+)-(5R,SS)-(6E,8E)-7-(p-tolylsulfinyl)dodeca-6,8-dien-5-ol (198987-20-1) → (2R,3R,1'S,SS)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane (884382-62-1)

Guidance literature:

Multi-step reaction with 3 steps

1: PPh₃; DIAD / tetrahydrofuran / 1.5 h / 0 °C

2: K₂CO₃ / methanol / 2 h / 0 °C

3: 76 percent / NaH; t-BuOOH; (t-BuO)2 / tetrahydrofuran / 1.17 h / 0 °C

With tert.-butylhydroperoxide; di-isopropyl azodicarboxylate; sodium hydride; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; 1: Mitsunobu reaction;

DOI:10.1016/j.tet.2005.12.024

Reference yield:

4-Nitro-benzoic acid (2E,4E)-(S)-1-butyl-3-((S)-toluene-4-sulfinyl)-octa-2,4-dienyl ester → (2R,3R,1'S,SS)-(E)-3-(1'-hydroxypentyl)-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane (884382-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / methanol / 2 h / 0 °C

2: 76 percent / NaH; t-BuOOH; (t-BuO)2 / tetrahydrofuran / 1.17 h / 0 °C

With tert.-butylhydroperoxide; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1016/j.tet.2005.12.024

upstream raw materials:

(+)-(5S,S_S)-(6E,8E)-7-(p-tolylsulfinyl)dodeca-6,8-dien-5-ol

(+)-(5R,S_S)-(6E,8E)-7-(p-tolylsulfinyl)dodeca-6,8-dien-5-ol

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