[1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester

Base Information

• Chemical Name: [1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester
• CAS No.: 153750-16-4
• Molecular Formula: C₂₂H₃₄O₆
• Molecular Weight: 394.508
• Mol file: 153750-16-4.mol

Synonyms:[1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester

Chemical Property of [1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester

There total 5 articles about [1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl 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: 99.0%

chloromethyl methyl ether (107-30-2) + [1R-(2-endo,3-exo,7-syn)]-7-hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester (153750-15-3) → [1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester (153750-16-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0957-4166(00)80084-1

Reference yield:

trimethylsilylcyclopentadiene (3559-74-8) → [1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester (153750-16-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diethylaluminum chloride / toluene; hexane / 1 h / -78 °C

1.2: 90 percent / toluene; hexane / 1 h / -78 °C

2.1: 97.4 percent / bromine / CH₂Cl₂ / 72 h / 20 °C

3.1: 88 percent / silver nitrate / 72 h / Heating

4.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 72 h / 20 °C

With bromine; diethylaluminium chloride; silver nitrate; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; toluene;

DOI:10.1248/cpb.52.1367

Reference yield:

di-L-menthyl fumarate (34675-24-6) → [1R-(2-endo,3-exo,7-syn)]-7-(methoxymethoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester (153750-16-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diethylaluminum chloride / toluene; hexane / 1 h / -78 °C

1.2: 90 percent / toluene; hexane / 1 h / -78 °C

2.1: 97.4 percent / bromine / CH₂Cl₂ / 72 h / 20 °C

3.1: 88 percent / silver nitrate / 72 h / Heating

4.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 72 h / 20 °C

With bromine; diethylaluminium chloride; silver nitrate; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; toluene;

DOI:10.1248/cpb.52.1367

upstream raw materials:

chloromethyl methyl ether

[1R-(2-endo,3-exo,7-syn)]-7-hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester

trimethylsilylcyclopentadiene

di-L-menthyl fumarate

Downstream raw materials:

[(1S,2S,3S,4R,7R)-2,3-Bis-(diphenyl-phosphinoylmethyl)-bicyclo[2.2.1]hept-7-yloxy]-acetic acid tert-butyl ester

{(1S,2S,3S,4R,7R)-2,3-Bis-[(diphenylphosphanyl)-methyl]-bicyclo[2.2.1]hept-7-yloxy}-acetic acid tert-butyl ester

(1S,2S,3S,4R,7R)-2,3-Bis-(diphenyl-phosphinoylmethyl)-bicyclo[2.2.1]heptan-7-ol

{(1S,2S,3S,4R,7R)-2,3-Bis-[(diphenylphosphanyl)-methyl]-bicyclo[2.2.1]hept-7-yloxy}-acetic acid