(-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Base Information

Chemical Name:(-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate
CAS No.:101046-90-6
Molecular Formula:C₂₀H₃₂O₄
Molecular Weight:336.472
Hs Code.:

Synonyms:(-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

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Chemical Property of (-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

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Technology Process of (-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

There total 6 articles about (-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-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: 80.0%

: 101046-89-3
(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

: 107-30-2
chloromethyl methyl ether

: 101046-90-6
(-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.) 0 deg C, 2.) room temperature, 10 h;

Reference yield:

: 93489-96-4
(-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

: 101046-90-6
(-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 37 percent / SeO₂, tBuOOH / CH₂Cl₂ / 1 h / Ambient temperature

2: 80 percent / Hunig base / 10 h / Ambient temperature

With tert.-butylhydroperoxide; selenium(IV) oxide; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1246/cl.1985.1131

Reference yield:

: 2216-51-5
(-)-menthol

: 101046-90-6
(-)-menthyl (1R,3S,5S)-3-methoxymethoxy-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / 4-(dimethylamino)pyridine (DMAP), dicyclohexylcarbodi-imide (DCC) / CH₂Cl₂ / 1.) 0 deg C, 2.) room temperature, 2.5 h

2: 1.) sodium 2-methylbutan-2-olate / 1.) toluene, 0 deg C; room temperature, 2 h, 2.) toluene, room temperature, 2 h

3: 37 percent / selenium dioxide, t-butylhydroperoxide / CH₂Cl₂ / 1 h

4: 80 percent / N-ethyl diisopropylamine (Huenig's base) / CH₂Cl₂ / 1.) 0 deg C, 2.) room temperature, 10 h

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; sodium tert-pentoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;