tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate

Base Information

• Chemical Name: tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate
• CAS No.: 155861-95-3
• Molecular Formula: C₂₁H₂₈O₆S
• Molecular Weight: 408.516
• Mol file: 155861-95-3.mol

Synonyms:tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate

Chemical Property of tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate

There total 2 articles about tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate 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: 75.0%

(+)-(R)-1-(p-tolylsulfinyl)-2-propanone (66536-78-5) + tert-Butyl ethyl 3-oxo-2-methyladipate (155861-94-2) → tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate (155861-95-3)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; 1.) 0 deg C, 30 min, 2.) r.t., 2 h;

DOI:10.1021/jo00093a022

Reference yield:

1-(tert-butyl) 6-ethyl 3-oxohexanedioate (93044-04-3) → tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate (155861-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / t-BuOK / 2-methyl-propan-2-ol / 1.) 25 deg C, 30 min, 2.) 20 min

2: 75 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

With n-butyllithium; potassium tert-butylate; diisopropylamine; In tetrahydrofuran; hexane; tert-butyl alcohol;

DOI:10.1021/jo00093a022

Reference yield: 60.0%

tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate (155861-95-3) → tert-Butyl <8(S),S(R)>-8-hydroxy-2-methyl-3,6-dioxo-9-(p-toluenesulfinyl)nonanoate (155861-96-4)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 0.25h;

DOI:10.1021/jo00093a022

upstream raw materials:

(+)-(R)-1-(p-tolylsulfinyl)-2-propanone

tert-Butyl ethyl 3-oxo-2-methyladipate

1-(tert-butyl) 6-ethyl 3-oxohexanedioate

Downstream raw materials:

tert-Butyl <8(S),S(R)>-8-hydroxy-2-methyl-3,6-dioxo-9-(p-toluenesulfinyl)nonanoate

2-[(S)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester

2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester