3,5-Hexadienoic acid, 2,4-dimethyl-2-[(1-oxopropyl)thio]-, phenylmethyl ester, (2R,3E)-

Base Information

• Chemical Name: 3,5-Hexadienoic acid, 2,4-dimethyl-2-[(1-oxopropyl)thio]-, phenylmethyl ester, (2R,3E)-
• CAS No.: 886733-89-7
• Molecular Formula: C18H22O3S
• Molecular Weight: 318.437
• Mol file: 886733-89-7.mol

Synonyms:

Chemical Property of 3,5-Hexadienoic acid, 2,4-dimethyl-2-[(1-oxopropyl)thio]-, phenylmethyl ester, (2R,3E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,5-Hexadienoic acid, 2,4-dimethyl-2-[(1-oxopropyl)thio]-, phenylmethyl ester, (2R,3E)-

There total 11 articles about 3,5-Hexadienoic acid, 2,4-dimethyl-2-[(1-oxopropyl)thio]-, 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: 75.0%

(R,E)-benzyl 2,4-dimethyl-2-(3-oxopropylthio)hexa-3,5-dienoate (886733-97-7) + propionyl chloride (79-03-8) → (R,E)-benzyl 2,4-dimethyl-2-(propionylthio)hexa-3,5-dienoate (886733-89-7)

Guidance literature:

(R,E)-benzyl 2,4-dimethyl-2-(3-oxopropylthio)hexa-3,5-dienoate; With caesium carbonate; In ethanol; at 4 ℃; for 0.333333h; Inert atmosphere;

propionyl chloride; With triethylamine; In dichloromethane; at 4 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.054

Reference yield: 38.0%

(R,E)-benzyl 2,4-dimethyl-2-(3-oxopropylthio)hexa-3,5-dienoate (886733-97-7) + propionyl chloride (79-03-8) → (R,E)-benzyl 2,4-dimethyl-2-(propionylthio)hexa-3,5-dienoate (886733-89-7) + (R,E)-benzyl 2,4-dimethyl-2-[(E,Z)-3-(propionyloxy)prop-2-enylthio]hexa-3,5-dienoate (1143584-04-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 4 - 40 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.054

Reference yield:

Caesium; (E)-(R)-2-benzyloxycarbonyl-4-methyl-hexa-3,5-diene-2-thiolate + propionyl chloride (79-03-8) → (R,E)-benzyl 2,4-dimethyl-2-(propionylthio)hexa-3,5-dienoate (886733-89-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tetlet.2006.02.058

upstream raw materials:

propionyl 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

Downstream raw materials:

(+)-thiolactomycin

Refernces

• 1、 Ohata, Kohei,Terashima, Shiro. "Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative". . p. 2787 - 2791. Retrieved 2007/10/03.