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

Base Information

• Chemical Name: (5R,S_S)-(6E,8E)-7-(p-tolylsulfinyl)-6,8-dodecadien-5-ol tert-butyldimethylsilyl ether
• CAS No.: 884382-53-0
• Molecular Formula: C₂₅H₄₂O₂SSi
• Molecular Weight: 434.759

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

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

Chemical Property:

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

There total 1 articles about (5R,S_S)-(6E,8E)-7-(p-tolylsulfinyl)-6,8-dodecadien-5-ol tert-butyldimethylsilyl ether 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (+)-(5R,SS)-(6E,8E)-7-(p-tolylsulfinyl)dodeca-6,8-dien-5-ol (198987-20-1) → (5R,SS)-(6E,8E)-7-(p-tolylsulfinyl)-6,8-dodecadien-5-ol tert-butyldimethylsilyl ether (884382-53-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 1.58333h;

DOI:10.1016/j.tet.2005.12.024

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:

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

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / KH; t-BuOOH; (t-BuO)2 / tetrahydrofuran / 96 h / 0 °C

2: 74 percent / magnesium monoperoxyphthalate hexahydrate / methanol / 2 h / 0 - 20 °C

With tert.-butylhydroperoxide; potassium hydride; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; methanol;

DOI:10.1016/j.tet.2005.12.024

upstream raw materials:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

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