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

Base Information

• Chemical Name: ethyl (-)-(R)_s-(1S,4S)-exo-2-methyl-endo-3-(p-tolylsulfinyl)bicyclo<2.2.1>hept-5-ene-endo-2-carboxylate
• CAS No.: 89919-52-8
• Molecular Formula: C₁₈H₂₂O₃S
• Molecular Weight: 318.437

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

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

Chemical Property:

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

There total 4 articles about ethyl (-)-(R)_s-(1S,4S)-exo-2-methyl-endo-3-(p-tolylsulfinyl)bicyclo<2.2.1>hept-5-ene-endo-2-carboxylate 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: 45.0%

ethyl (-)-(Z)-(R)s-2-methyl-3-(p-tolylsulfinyl)propenoate (89764-37-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (2S,3S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester + 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) + (1S,2R,3R,4R)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

Guidance literature:

at 90 ℃; for 5h; Product distribution; Mechanism; in sealed tube;

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

Reference yield: 31.0%

ethyl (-)-(Z)-(R)s-2-methyl-3-(p-tolylsulfinyl)propenoate (89764-37-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 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) + ethyl (+)-(R)s-(1R,4S)-endo-2-methyl-exo-3-(p-tolylsulfinyl)bicyclo<2.2.1>hept-5-ene-exo-2-carboxylate (89919-54-0) + ethyl (+)-(R)s-(1R,4S)-exo-2-methyl-endo-3-(p-tolylsulfinyl)bicyclo<2.2.1>hept-5-ene-endo-2-carboxylate

Guidance literature:

at 90 ℃; for 5h;

DOI:10.1246/bcsj.61.467

Reference yield:

2-oxo-propionic acid ethyl ester (617-35-6) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 57 percent / 5 h / 90 °C

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1246/bcsj.61.467

upstream raw materials:

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

cyclopenta-1,3-diene

2-oxo-propionic acid ethyl ester

diethyl p-tolylsulfinylmethylphosphonate

Downstream raw materials:

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

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

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

(-)-(1S,4R)-endo-2-methyl-3-oxobicyclo<2.2.1>heptane-exo-2-carboxaldehyde

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