<3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene

Base Information

• Chemical Name: <3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene
• CAS No.: 110416-47-2
• Molecular Formula: C₁₈H₂₂O₃S
• Molecular Weight: 318.437
• Mol file: 110416-47-2.mol

Synonyms:<3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene

Chemical Property of <3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene

There total 4 articles about <3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene 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:

2-methyl-2-cyclopenten-1-one (1120-73-6) → <3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene (110416-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 5 min

2: tetrahydrofuran / -78 °C

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00381a002

Reference yield:

(R)-(+)-allyl p-tolyl sulphoxide (89708-79-2) → <3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene (110416-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 5 min

2: tetrahydrofuran / -78 °C

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00381a002

Reference yield:

(S)-2-Methyl-3-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-cyclopent-1-enol + acetyl chloride (75-36-5) → <3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene (110416-47-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; Yield given;

DOI:10.1021/jo00381a002

upstream raw materials:

2-methyl-2-cyclopenten-1-one

(R)-(+)-allyl p-tolyl sulphoxide

acetyl chloride

Downstream raw materials:

<1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one

<1(R),5(S),8(S))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one

Acetic acid (S)-2-methyl-3-((E)-3-p-tolylsulfanyl-allyl)-cyclopent-1-enyl ester