(+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one

Base Information

• Chemical Name: (+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one
• CAS No.: 158833-98-8
• Molecular Formula: C₂₀H₃₄O₃SSi
• Molecular Weight: 382.64
• Mol file: 158833-98-8.mol

Synonyms:(+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one

Chemical Property of (+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one

There total 9 articles about (+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one 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: 94.0%

(R)-methyl p-tolyl sulfoxide (1519-39-7) + (+)-methyl (5S)-5-<(tert-butyldimethylsilyl)oxy>hexanoate (127953-97-3) → (+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one (158833-98-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)77089-4

Reference yield:

Methyl p-tolyl sulfoxide (934-72-5) + (+)-methyl (5S)-5-<(tert-butyldimethylsilyl)oxy>hexanoate (127953-97-3) → (+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one (158833-98-8)

Guidance literature:

Methyl p-tolyl sulfoxide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - -30 ℃; for 0.5h; Inert atmosphere; Reflux;

(+)-methyl (5S)-5-<(tert-butyldimethylsilyl)oxy>hexanoate; In tetrahydrofuran; at -78 ℃;

Reference yield:

(S)-5-oxo-6-(p-toluenesulfinyl)hexanoic acid (799247-36-2) → (+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one (158833-98-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetone / Reflux

2.1: zinc dibromide / tetrahydrofuran / Reflux

3.1: 1H-imidazole / N,N-dimethyl-formamide / Reflux; Inert atmosphere

3.2: Raney nickel

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 - -30 °C / Inert atmosphere; Reflux

4.2: -78 °C

With 1H-imidazole; potassium carbonate; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

upstream raw materials:

(R)-methyl p-tolyl sulfoxide

(+)-methyl (5S)-5-<(tert-butyldimethylsilyl)oxy>hexanoate

Methyl p-tolyl sulfoxide

(S)-5-oxo-6-(p-toluenesulfinyl)hexanoic acid

Downstream raw materials:

(+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol