2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester

Base Information

• Chemical Name: 2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester
• CAS No.: 303044-43-1
• Molecular Formula: C₁₇H₂₁ClO₅
• Molecular Weight: 340.804
• Mol file: 303044-43-1.mol

Synonyms:2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester

Chemical Property of 2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester

There total 10 articles about 2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-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: 80.0%

(+)-(3R,4R,6R)-6-(hydroxy)-3,4-(oxiranyl)-hept-1-ene (303044-38-4) + 2-(chloromethyl)-4,6-dimethoxy-benzoic acid (303044-37-3) → 2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester (303044-43-1)

Guidance literature:

2-(chloromethyl)-4,6-dimethoxy-benzoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 25 ℃; for 1h;

(+)-(3R,4R,6R)-6-(hydroxy)-3,4-(oxiranyl)-hept-1-ene; With triethylamine; dmap; In dichloromethane; N,N-dimethyl-formamide; at 25 ℃; for 12h; Further stages.;

DOI:10.1021/ol0063252

Reference yield:

(+)-(3R,4R,6R)-6-(hydroxy)-3,4-(oxiranyl)-hept-1-ene (303044-38-4) + 2-chloromethyl-4,6-dimethoxy-benzoyl chloride → 2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester (303044-43-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1021/ja011364+

Reference yield:

3,5-dimethoxybenzyl alcohol (705-76-0) → 2-Chloromethyl-4,6-dimethoxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester (303044-43-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: POCl₃ / 0.33 h / 25 °C

1.2: 93 percent / 2 h / 25 - 75 °C

2.1: NaClO₂; sulfamic acid / tetrahydrofuran; H₂O; dimethylsulfoxide / 0.33 h / 0 °C

3.1: (COCl)2; DMF / CH₂Cl₂ / 1 h / 25 °C

4.1: 0.47 g / Et₃N; DMAP / CH₂Cl₂ / 12 h / 25 °C

With dmap; sodium chlorite; oxalyl dichloride; aminosulfonic acid; triethylamine; N,N-dimethyl-formamide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/ja011364+

upstream raw materials:

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

2-(chloromethyl)-4,6-dimethoxy-benzoic acid

3,5-dimethoxybenzyl alcohol

2-(chloromethyl)-4,6-dimethoxy-benzaldehyde

Downstream raw materials:

2,4-Dimethoxy-6-[((1E,3E)-2-penta-1,3-dienyl)-[1,3]dithian-2-ylmethyl]-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester