(+)-(3R,4S,R_S)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone

Base Information

• Chemical Name: (+)-(3R,4S,R_S)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone
• CAS No.: 110968-91-7
• Molecular Formula: C₁₈H₂₂O₃S
• Molecular Weight: 318.437

Synonyms:(+)-(3R,4S,R_S)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone

Chemical Property of (+)-(3R,4S,R_S)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone

Chemical Property:

Purity/Quality:

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Technology Process of (+)-(3R,4S,R_S)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone

There total 2 articles about (+)-(3R,4S,R_S)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone 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:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (+)-(3R,4S,RS)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone (110968-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / 1.) diisopropylamine/n-butyl-lithium, 2.) lithium hydride / tetrahydrofuran; hexane / 0.08 h / -78 °C

2: 1.) LDA / 1.) THF, -78 deg C, 3 min; 2.) rt., neat, 2 d

With n-butyllithium; lithium hydride; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane;

Reference yield:

(+)-(R)-3-<(4-methylphenyl)sulphinyl>propionic acid (90334-31-9) + 1-cyclohexenyl methyl ketone (932-66-1) → (+)-(E)-4-(cyclohex-1-enyl)-4-hydroxy-2-pent-2-enoic acid (110969-08-9) + (+)-(3S,4R,RS)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone (110968-90-6) + (+)-(3R,4R,RS)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone (110968-92-8) + (+)-(3R,4S,RS)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone (110968-91-7)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -78 deg C, 3 min; 2.) rt., neat, 2 d;

Reference yield: 88.0%

(+)-(3R,4S,RS)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylsulphinyl)-γ-butyrolactone (110968-91-7) → (4R,5S)-5-Cyclohex-1-enyl-5-methyl-4-p-tolylsulfanyl-dihydro-furan-2-one (110968-99-5)

Guidance literature:

With trifluoroacetic anhydride; sodium iodide; In acetone; at -50 - -20 ℃; for 0.333333h;

upstream raw materials:

(+)-(R)-3-<(4-methylphenyl)sulphinyl>propionic acid

1-cyclohexenyl methyl ketone

(R)-methyl p-tolyl sulfoxide

Downstream raw materials:

(+)-(R)-4-(cyclohex-1-enyl)pentan-4-olide

(+)-(R)-5-(cyclohex-1-enyl)-5-methylfuran-2(5H)-one

(4R,5S)-5-Cyclohex-1-enyl-5-methyl-4-p-tolylsulfanyl-dihydro-furan-2-one

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