(1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: (1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester
• CAS No.: 120410-03-9
• Molecular Formula: C₁₈H₂₄O₃S
• Molecular Weight: 320.453
• Mol file: 120410-03-9.mol

Synonyms:(1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Chemical Property of (1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

There total 5 articles about (1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid 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: 100.0%

ethyl (-)-(R)s-(1S,4S)-exo-2-methyl-endo-3-(p-tolylsulfinyl)bicyclo<2.2.1>hept-5-ene-endo-2-carboxylate (89919-52-8) → (1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (120410-03-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; for 7h; Ambient temperature;

DOI:10.1246/bcsj.61.467

Reference yield: 69.0%

(1R,2R,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (89919-51-7) → (1S,2R,3S,4R)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (89764-39-6,89826-17-5,120410-03-9)

Guidance literature:

With hydrogen; catalytically hidrogenated;

DOI:10.1016/S0040-4039(01)91155-4

Reference yield:

2-oxo-propionic acid ethyl ester (617-35-6) → (1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (120410-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 33 percent / n-BuLi / tetrahydrofuran; hexane / 0.33 h / -80 °C

2: 57 percent / 5 h / 90 °C

3: 100 percent / H₂, 10percent Pd on carbon / ethanol / 7 h / Ambient temperature

With palladium on activated charcoal; n-butyllithium; hydrogen; In tetrahydrofuran; ethanol; hexane;

DOI:10.1246/bcsj.61.467

upstream raw materials:

ethyl (-)-(R)_s-(1S,4S)-exo-2-methyl-endo-3-(p-tolylsulfinyl)bicyclo<2.2.1>hept-5-ene-endo-2-carboxylate

2-oxo-propionic acid ethyl ester

ethyl (-)-(Z)-(R)_s-2-methyl-3-(p-tolylsulfinyl)propenoate

diethyl p-tolylsulfinylmethylphosphonate

Downstream raw materials:

ethyl (-)-(1R,4S)-exo-2-methyl-endo-3-(p-tlylthio)bicyclo<2.2.1>heptane-endo-2-carboxylate

(1S,2R,3S,4R)-2-Methyl-3-p-tolylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester