(-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate

Base Information

• Chemical Name: (-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate
• CAS No.: 121611-76-5
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.312
• Mol file: 121611-76-5.mol

Synonyms:(-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate

Chemical Property of (-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate

There total 9 articles about (-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate 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: 90.0%

(-)-(1R,RS)-2-benzyl 3-methyl 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate (121611-75-4) → (-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate (121611-76-5)

Guidance literature:

With diazabicyclo<5.4.0>undecene; In benzene; at 50 ℃; for 12h;

Reference yield:

(SS)-2-Benzyl 3-methyl 2-p-(tolylsulfinyl)bicyclo<2.2.1>hept-5-ene-2,3-dicarboxylate → (-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate (121611-76-5) + (+)-(1S,4R)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 70 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00085a043

Reference yield:

(1R,2R,3S,4S)-2-((R)-Toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-benzyl ester 3-methyl ester → (-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate (121611-76-5) + (+)-(1S,4R)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 70 ℃; Title compound not separated from byproducts;

DOI:10.1021/jo00085a043

upstream raw materials:

(-)-(1R,R_S)-2-benzyl 3-methyl 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate

(1R,2R,3S,4S)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester

(+)-(1R,R_S)-3-methyl hydrogen 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate

dimethyl (R_S)-2-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)maleate

Downstream raw materials:

(-)-2-benzyl 3-methyl-5-exo,6-exo-(isopropylidenedioxy)bicyclo<2.2.1>hept-2-ene-2,3-dicarboxylate