methyl 6-[(R)-(4-methylphenyl)sulfinyl]-3,5-dioxohexanoate

Base Information

• Chemical Name: methyl 6-[(R)-(4-methylphenyl)sulfinyl]-3,5-dioxohexanoate
• CAS No.: 171523-66-3
• Molecular Formula: C14H16O5S
• Molecular Weight: 296.344
• DSSTox Substance ID: DTXSID30445187
• Wikidata: Q82263537
• Mol file: 171523-66-3.mol

Synonyms:171523-66-3;methyl 6-[(R)-(4-methylphenyl)sulfinyl]-3,5-dioxohexanoate;SCHEMBL7759008;DTXSID30445187

Chemical Property of methyl 6-[(R)-(4-methylphenyl)sulfinyl]-3,5-dioxohexanoate

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 296.07184478
• Heavy Atom Count: 20
• Complexity: 396

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)CC(=O)CC(=O)CC(=O)OC
• Isomeric SMILES: CC1=CC=C(C=C1)[S@](=O)CC(=O)CC(=O)CC(=O)OC

Technology Process of methyl 6-[(R)-(4-methylphenyl)sulfinyl]-3,5-dioxohexanoate

There total 1 articles about methyl 6-[(R)-(4-methylphenyl)sulfinyl]-3,5-dioxohexanoate 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: 68.0%

3,5-dioxohexanoic acid methyl ester (29736-80-9) + (-)-menthyl p-toluenesulfinate (1517-82-4) → (+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate (171523-66-3)

Guidance literature:

With tert.-butyl lithium; sodium hydride; In tetrahydrofuran; pentane; at 0 ℃; for 0.666667h;

DOI:10.1021/jo00129a018

Reference yield: 45.0%

(+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate (171523-66-3) → (+)-<5(S),S(R)> methyl 3-oxo-5-hydroxy-6-(p-tolylsulfinyl) hexanoate (171523-67-4)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/0957-4166(95)00356-T

Reference yield:

(+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate (171523-66-3) → (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate (191854-41-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -78 °C

2: 1.) Et₂BOMe, 2.) NaBH₄ / 1.) THF, MeOH, -78 deg C, 20 min, 2.) -78 deg C, 4 h

3: 98 percent / p-TsOH / p-TsOH / acetone / 3 h / Ambient temperature

4: 97 percent / AcONa / 10 h / 135 °C

With sodium tetrahydroborate; diethyl methoxy borane; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; toluene;

DOI:10.1021/jo00129a018

upstream raw materials:

3,5-dioxohexanoic acid methyl ester

(-)-menthyl p-toluenesulfinate

Downstream raw materials:

(+)-<5(S),S(R)> methyl 3-oxo-5-hydroxy-6-(p-tolylsulfinyl) hexanoate

(3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate

(+)-<3(R),5(S),S(R)> methyl 3,5-dihydroxy-6-(p-tolylsulfinyl) hexanoate

(+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate