(R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide

Base Information

• Chemical Name: (R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide
• CAS No.: 817161-08-3
• Molecular Formula: C₂₄H₃₄O₂SSi
• Molecular Weight: 414.684
• Mol file: 817161-08-3.mol

Synonyms:(R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide

Chemical Property of (R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide

There total 1 articles about (R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide 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: 87.0%

phenylzinc(II) bromide (38111-44-3) + (R)-5-[[tert-butyl(dimethyl)silyl]oxy]-1-pentynyl p-tolyl sulfoxide (817161-04-9) → (R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide (817161-08-3)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo048747l

Reference yield: 96.0%

(R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide (817161-08-3) → (Z)-5-methyl-6-[(R)-(p-tolyl)sulfinyl]-5-hexen-1-ol (817161-11-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1021/jo048747l

Reference yield:

(R)-[(E)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1-pentenyl] p-tolyl sulfoxide (817161-08-3) → (2S)-2-methyl-2-[(R)-(p-tolyl)sulfinylmethyl]tetrahydrofuran

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

2: 89 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 2: Michael addition;

DOI:10.1021/jo048747l

upstream raw materials:

phenylzinc(II) bromide

(R)-5-[[tert-butyl(dimethyl)silyl]oxy]-1-pentynyl p-tolyl sulfoxide

Downstream raw materials:

(Z)-5-methyl-6-[(R)-(p-tolyl)sulfinyl]-5-hexen-1-ol