(1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Base Information

• Chemical Name: (1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester
• CAS No.: 167640-38-2
• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.709

Synonyms:(1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Chemical Property of (1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Chemical Property:

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Technology Process of (1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

There total 1 articles about (1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) 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: 70.0%

di-L-menthyl fumarate (34675-24-6) + cyclohexa-1,3-diene (1165952-91-9) → (1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (167640-38-2)

Guidance literature:

With aluminium trichloride; In toluene; at -78 ℃; for 2h;

DOI:10.1002/hlca.19940770802

Reference yield: 27.0%

methanol (67-56-1) + (1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (167640-38-2) → dimethyl (2S,3S)-bicyclo<2.2.2>oct-5-ene-2C(6),3C(8)-dicarboxylate (40335-59-9) + (1'R,2'S,5'R)-menthylC(6) methylC(8) (2S,3S)-bicyclo<2.2.2>oct-5-ene-2C(6),3C(8)-dicarboxylate + methylC(6) (1'R,2'S,5'R)-menthylC(8) (2S,3S)-bicyclo<2.2.2>oct-5-ene-2C(6),3C(8)-dicarboxylate

Guidance literature:

With methanesulfonic acid; at 60 ℃; for 336h; Yields of byproduct given;

DOI:10.1002/hlca.19940770802

Reference yield:

(1S,2S,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (167640-38-2) → (2S,3S)-α,α,α',α'-tetraphenylbicyclo<2.2.2>octan-2C(6),3C(8)-dimethanol

Guidance literature:

Multi-step reaction with 3 steps

1: 27 percent / MeSO₃H / 336 h / 60 °C

2: 83 percent / tetrahydrofuran

3: 90 percent / H₂ / 10percent Pd/C / diethyl ether / 2 h / Ambient temperature

With methanesulfonic acid; hydrogen; palladium on activated charcoal; In tetrahydrofuran; diethyl ether;

DOI:10.1002/hlca.19940770802

upstream raw materials:

di-L-menthyl fumarate

cyclohexa-1,3-diene

Downstream raw materials:

dimethyl (2S,3S)-bicyclo<2.2.2>oct-5-ene-2^C(6),3^C(8)-dicarboxylate

(2S,3S)-α,α,α',α'-tetraphenylbicyclo<2.2.2>oct-5-ene-2^C(6),3^C(8)-dimethanol

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