(+)-(1R,S_S)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate

Base Information

• Chemical Name: (+)-(1R,S_S)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate
• CAS No.: 110522-48-0
• Molecular Formula: C₂₃H₃₁NO₃S
• Molecular Weight: 401.57

Synonyms:(+)-(1R,S_S)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate

Chemical Property of (+)-(1R,S_S)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (+)-(1R,S_S)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate

There total 5 articles about (+)-(1R,S_S)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-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: 95.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + (SS)(Z)-menthyl 3-(2-pyridylsulphinyl)acylate (105802-70-8) → (+)-(1R,SS)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate (110522-48-0)

Guidance literature:

With diethylaluminium chloride; In hexane; dichloromethane; at -78 ℃;

DOI:10.1021/jo951767q

Reference yield: 92.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + menthyl (R)s-3-(2-pyridylsulfinyl)propenoate (105802-70-8,105880-25-9) → (1S,2S,3S,4R)-3-((R)-Pyridine-2-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (110522-48-0,110550-20-4)

Guidance literature:

DOI:10.1246/cl.1987.185

Reference yield:

(Z)-3-(Pyridin-2-ylsulfanyl)-acrylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (120424-54-6,120424-55-7) → (+)-(1R,SS)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate (110522-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

2: 95 percent / Et₂AlCl / hexane; CH₂Cl₂ / -78 °C

With diethylaluminium chloride; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane;

DOI:10.1021/jo951767q

upstream raw materials:

cyclopenta-1,3-diene

(S_S)(Z)-menthyl 3-(2-pyridylsulphinyl)acylate

(Z)-3-(Pyridin-2-ylsulfanyl)-acrylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

2-Sulfanylpyridine

Downstream raw materials:

(1S,2R,6S,7S,8R,9R)-4,4-Dimethyl-9-((S)-pyridine-2-sulfinyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(-)-(1S)-menthyl 5-exo,6-exo-(isopropylidenedioxy)-3-endo-(2-pyridylsulphonyl)bicyclo<2.2.1>heptane-2-endo-carboxylate

(-)-(R_S)-menthyl 5-exo,6-exo-(isopropylidenedioxy)-3-endo-(2-pyridylsulphinyl)-bicyclo<2.2.1>heptane-2-carboxylate

(-)-(1R)-menthyl 5-exo,6-exo-(isopropylidenedioxy)-3-endo-(2-pyridinylsulphonyl)bicyclo<2.2.1>heptane-2-endo-carboxylate

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