2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester

Base Information

• Chemical Name: 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester
• CAS No.: 754201-26-8
• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.497
• Mol file: 754201-26-8.mol

Synonyms:2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester

Chemical Property of 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester

There total 20 articles about 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester 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:

orsellinic acid (480-64-8) → 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester (754201-26-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C

2.1: 91 percent / iPr₂NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C

3.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

3.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C

4.1: aq. H₂O₂ / various solvent(s) / 3 h / 23 °C

5.1: toluene / 1 h / 80 °C

With di-isopropyl azodicarboxylate; tri(m-chlorophenyl)-phosphine; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1.1: Mitsunobu esterification;

DOI:10.1002/chem.200500160

Reference yield:

N-methoxy-N-methyl-2-(phenylthio)pent-4-enamide (754201-16-6) → 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester (754201-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

1.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C

2.1: aq. H₂O₂ / various solvent(s) / 3 h / 23 °C

3.1: toluene / 1 h / 80 °C

With dihydrogen peroxide; lithium diisopropyl amide; In tetrahydrofuran; toluene;

DOI:10.1002/chem.200500160

Reference yield:

(S)-1-((2R,3S)-3-Vinyl-oxiranyl)-propan-2-ol (754201-30-4) → 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester (754201-26-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C

2.1: 91 percent / EtiPr₂N; TBAI / dimethylformamide / 3 h / 80 °C

3.1: LDA / tetrahydrofuran / -78 °C

3.2: 81 percent / tetrahydrofuran / cooling

4.1: aq. H₂O₂ / various solvent(s) / 3 h / 23 °C

5.1: toluene / 1 h / 80 °C

With di-isopropyl azodicarboxylate; tri(m-chlorophenyl)-phosphine; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1.1: Mitsunobu esterification;

DOI:10.1002/chem.200500160

upstream raw materials:

(3R,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxy)-3-chloro-hept-1-en-4-ol

(S)-4-penten-2-ol

orsellinic acid

(3R,4R,6S)-6-(hydroxy)-3,4-(oxiranyl)hept-1-ene