phenyl (3S,S_S)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate

Base Information

• Chemical Name: phenyl (3S,S_S)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate
• CAS No.: 259142-47-7
• Molecular Formula: C₂₀H₁₈O₅S
• Molecular Weight: 370.426
• Mol file: 259142-47-7.mol

Synonyms:phenyl (3S,S_S)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate

Chemical Property of phenyl (3S,S_S)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl (3S,S_S)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate

There total 1 articles about phenyl (3S,S_S)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate 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: 81.0%

1-phenoxy-1-trimethylsilyloxyethene (111061-31-5) + 3-((S)-Toluene-4-sulfinyl)-furan-2-carbaldehyde (159812-85-8) → phenyl (3R,SS)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate + phenyl (3S,SS)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate (259142-47-7)

Guidance literature:

With neodymium(III) trifluoromethanesufonate; In tetrahydrofuran; for 5h;

DOI:10.1021/jo991307n

Reference yield: 66.0%

phenyl (3S,SS)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate (259142-47-7) → (1S)-3-hydroxy-1-[3-(p-tolylsulfanyl)-2-furyl]propan-1-ol (259142-49-9) + (1S,SS)-3-hydroxy-1-[3-(p-tolylsulfinyl)-2-furyl]propan-1-ol (259142-48-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1021/jo991307n

Reference yield:

phenyl (3S,SS)-3-hydroxy-3-[3-(p-tolylsulfinyl)-2-furyl]propanoate (259142-47-7) → 6-hydroxy-2-phenethyl-4-p-tolylsulfanyl-6H-pyran-3-one (259142-52-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 8 percent / DIBALH / CH₂Cl₂ / 1.5 h / -78 °C

2: 84 percent / pyridine / 3 h / 0 °C

3: 75 percent / CuI / diethyl ether; cyclohexane / 1.5 h / -30 - 0 °C

4: 100 percent / N-bromosuccinimide; AcOK / tetrahydrofuran; H₂O / 0.33 h / 0 °C

With pyridine; N-Bromosuccinimide; copper(l) iodide; potassium acetate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; water; 1: Reduction / 2: Tosylation / 3: Substitution / 4: Oxidation;

DOI:10.1021/jo991307n

upstream raw materials:

1-phenoxy-1-trimethylsilyloxyethene

3-((S)-Toluene-4-sulfinyl)-furan-2-carbaldehyde

Downstream raw materials:

(1S)-3-hydroxy-1-[3-(p-tolylsulfanyl)-2-furyl]propan-1-ol

(1S,S_S)-3-hydroxy-1-[3-(p-tolylsulfinyl)-2-furyl]propan-1-ol

(1S)-3-phenyl-1-[3-(p-tolylsulfanyl)-2-furyl]propan-1-ol

6-hydroxy-2-phenethyl-4-p-tolylsulfanyl-6H-pyran-3-one