(8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone

Base Information

• Chemical Name: (8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone
• CAS No.: 1127424-80-9
• Molecular Formula: C₂₂H₂₅NO₂S₂
• Molecular Weight: 399.578

Synonyms:(8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone

Chemical Property of (8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone

Chemical Property:

Purity/Quality:

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Technology Process of (8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone

There total 1 articles about (8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone 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%

(8aS,1'R,2'S,4'S)-8-(2'-methyl-6'-oxo-4'-(phenylsulfanyl)cyclohexanecarbonyl)-1,5,6,8a-tetrahydro-2H-indolizin-3-one (1127424-78-5) → (8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone (1127424-80-9)

Guidance literature:

With Lawessons reagent; In dichloromethane; toluene; at 65 ℃; for 0.25h;

DOI:10.1021/ol900032h

Reference yield: 63.0%

(8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone (1127424-80-9) → (5S)-6-((S)-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)-5-methylcyclohex-2-enone (1027172-71-9)

Guidance literature:

(8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone; With trimethoxonium tetrafluoroborate; In acetonitrile; at 20 ℃; for 1h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 1h;

DOI:10.1021/ol900032h

Reference yield:

(8aS,2'R,3'S,5'S)-(3-methyl-5-phenylsulfanyl)-2'-(3-thioxo-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)cyclohexanone (1127424-80-9) + trimethoxonium tetrafluoroborate (420-37-1) → BF4(1-)*C17H22NO2S(1+)

Guidance literature:

In acetonitrile; at 4 - 20 ℃;

DOI:10.1002/chem.200901843

upstream raw materials:

(8aS,1'R,2'S,4'S)-8-(2'-methyl-6'-oxo-4'-(phenylsulfanyl)cyclohexanecarbonyl)-1,5,6,8a-tetrahydro-2H-indolizin-3-one

Downstream raw materials:

(5S)-6-((S)-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)-5-methylcyclohex-2-enone

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