(1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Base Information

Chemical Name:(1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
CAS No.:1095263-19-6
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:(1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

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Chemical Property of (1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

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Technology Process of (1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

There total 1 articles about (1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-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: 89.0%

: 153750-15-3
[1R-(2-endo,3-exo,7-syn)]-7-hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester

: 1095263-19-6
(1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Guidance literature:: [1R-(2-endo,3-exo,7-syn)]-7-hydroxybicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid methyl (1R)-menthyl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1002/anie.200803284

Reference yield: 92.0%

: 1095263-19-6
(1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

: 149-73-5
trimethyl orthoformate

: 1095262-99-9
(1R,2S,3S,4S)-2-(l(-)-menthyl) 3-methyl 7-bis(methoxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 50 ℃; for 1.5h; Inert atmosphere;
DOI:10.1002/anie.200803284

Reference yield: 79.0%

: 1095263-19-6
(1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

: 20781-20-8
2,4-Dimethoxybenzylamine

: 74739-36-9
1-isocyano-2-nitrobenzene

: 1259807-01-6
2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 3-methyl (1R,2S,3S,4S,7R)-7-(2,4-dimethoxybenzylamino)-7-(2-nitrophenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Guidance literature:: (1R,2S,3S,4S)-2-(L(-)-menthyl) 3-methyl 7-oxobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate; 2,4-Dimethoxybenzylamine; With toluene-4-sulfonic acid; In toluene; for 3h; Reflux; Inert atmosphere;

1-isocyano-2-nitrobenzene; With trifluoroacetic acid; In methanol; at -78 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol102577q