(2R,3R,1'R,S_S)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

Base Information

• Chemical Name: (2R,3R,1'R,S_S)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane
• CAS No.: 884382-60-9
• Molecular Formula: C₂₅H₄₂O₃SSi
• Molecular Weight: 450.758

Synonyms:(2R,3R,1'R,S_S)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

Chemical Property of (2R,3R,1'R,S_S)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

Chemical Property:

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Technology Process of (2R,3R,1'R,S_S)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane

There total 3 articles about (2R,3R,1'R,S_S)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-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: 38.0%

(5R,SS)-(6E,8E)-7-(p-tolylsulfinyl)-6,8-dodecadien-5-ol tert-butyldimethylsilyl ether (884382-53-0) → (1'R)-(E)-3-[1'-(tert-butyldimethylsilyloxy)pentyl]-2-(1-pentenyl)-2-(p-tolylsulfonyl)oxirane + (2R,3R,1'R,SS)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane (884382-60-9)

Guidance literature:

With tert.-butylhydroperoxide; potassium hydride; In tetrahydrofuran; at 0 ℃; for 96h;

DOI:10.1016/j.tet.2005.12.024

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3R,1'R,SS)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane (884382-60-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / imidazole / CH₂Cl₂ / 1.58 h / 0 - 20 °C

2: 38 percent / KH; t-BuOOH; (t-BuO)2 / tetrahydrofuran / 96 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; potassium hydride; In tetrahydrofuran; dichloromethane;

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'R,SS)-(E)-3-[1'-(tert-butyldimethylsilyloxy)-n-pentyl]-2-(1-pentenyl)-2-(p-tolylsulfinyl)oxirane (884382-60-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / imidazole / CH₂Cl₂ / 1.58 h / 0 - 20 °C

2: 38 percent / KH; t-BuOOH; (t-BuO)2 / tetrahydrofuran / 96 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; potassium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.12.024

upstream raw materials:

(5R,S_S)-(6E,8E)-7-(p-tolylsulfinyl)-6,8-dodecadien-5-ol tert-butyldimethylsilyl ether

tert-butyldimethylsilyl chloride

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

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