(2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane

Base Information

• Chemical Name: (2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane
• CAS No.: 1345024-17-0
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• Mol file: 1345024-17-0.mol

Synonyms:(2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane

Chemical Property of (2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane

There total 3 articles about (2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane 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: 95.0%

1,3-dimethoxy-2-methyl-5-[(Z)-prop-1-enyl]benzene (1345024-11-4) → (2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane (1345024-17-0)

Guidance literature:

With (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; at -78 - 20 ℃; optical yield given as %ee;

DOI:10.1055/s-0030-1260166

Reference yield:

2-(3,5-dimethoxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1345024-09-0) → (2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane (1345024-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 16 h / 45 °C / Inert atmosphere

2: (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid / ethanol; dichloromethane / -78 - 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); potassium carbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; water; toluene; 1: Suzuki cross-coupling / 2: Katsuki-Jacobsen epoxiodation;

DOI:10.1055/s-0030-1260166

Reference yield:

2,6-dimethoxytoluene (5673-07-4) → (2R,3S)-2-(3,5-dimethoxy-4-methylphenyl)-3-methyloxirane (1345024-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / octane / 0.25 h / 20 °C

1.2: 72 h / 125 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 16 h / 45 °C / Inert atmosphere

3.1: (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid / ethanol; dichloromethane / -78 - 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); potassium carbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 4,4'-di-tert-butyl-2,2'-bipyridine; In octane; ethanol; dichloromethane; water; toluene; 2.1: Suzuki cross-coupling / 3.1: Katsuki-Jacobsen epoxiodation;

DOI:10.1055/s-0030-1260166

upstream raw materials:

2-(3,5-dimethoxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1,3-dimethoxy-2-methyl-5-[(Z)-prop-1-enyl]benzene

2,6-dimethoxytoluene

Downstream raw materials:

(1S,2S)-1-(3,5-dimethoxy-4-methylphenyl)propane-1,2-diol