3,5-Hexadienoic acid, 2-(acetylthio)-2,4-dimethyl-, phenylmethyl ester, (2R,3E)-

Base Information

• Chemical Name: 3,5-Hexadienoic acid, 2-(acetylthio)-2,4-dimethyl-, phenylmethyl ester, (2R,3E)-
• CAS No.: 886733-90-0
• Molecular Formula: C₁₇H₂₀O₃S
• Molecular Weight: 304.41
• Mol file: 886733-90-0.mol

Synonyms:

Chemical Property of 3,5-Hexadienoic acid, 2-(acetylthio)-2,4-dimethyl-, phenylmethyl ester, (2R,3E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-Hexadienoic acid, 2-(acetylthio)-2,4-dimethyl-, phenylmethyl ester, (2R,3E)-

There total 9 articles about 3,5-Hexadienoic acid, 2-(acetylthio)-2,4-dimethyl-, phenylmethyl ester, (2R,3E)- 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:

Caesium; (E)-(R)-2-benzyloxycarbonyl-4-methyl-hexa-3,5-diene-2-thiolate + acetyl chloride (75-36-5) → (R,E)-benzyl 2,4-dimethyl-2-(acetylthio)hexa-3,5-dienoate (886733-90-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tetlet.2006.02.058

Reference yield:

(R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one (886733-93-3) → (R,E)-benzyl 2,4-dimethyl-2-(acetylthio)hexa-3,5-dienoate (886733-90-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / NaHMDS; HMPA / tetrahydrofuran / 2 h / -78 - 0 °C

2: 83 percent / Ti(OiPr)4 / 70 °C

3: 97 percent / aq. HCl / tetrahydrofuran / 20 °C

4: Cs₂CO₃ / ethanol / 0 °C

5: Et₃N / CH₂Cl₂ / 0 °C

With titanium(IV) isopropylate; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane; caesium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.02.058

Reference yield:

C13H20O3 → (R,E)-benzyl 2,4-dimethyl-2-(acetylthio)hexa-3,5-dienoate (886733-90-0)

Guidance literature:

Multi-step reaction with 6 steps

1: LiCl / tetrahydrofuran / 20 °C

2: 74 percent / NaHMDS; HMPA / tetrahydrofuran / 2 h / -78 - 0 °C

3: 83 percent / Ti(OiPr)4 / 70 °C

4: 97 percent / aq. HCl / tetrahydrofuran / 20 °C

5: Cs₂CO₃ / ethanol / 0 °C

6: Et₃N / CH₂Cl₂ / 0 °C

With titanium(IV) isopropylate; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane; caesium carbonate; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.02.058

upstream raw materials:

acetyl chloride

(R,E)-benzyl 2,4-dimethyl-2-(3-oxopropylthio)hexa-3,5-dienoate

(R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one

(R,E)-benzyl 2-(3,3-dimethoxypropylthio)-2,4-dimethylhexa-3,5-dienoate