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

Base Information

• Chemical Name: (1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,R_S)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide
• CAS No.: 132345-18-7
• Molecular Formula: C₂₆H₃₁NO₄S
• Molecular Weight: 453.602

Synonyms:(1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,R_S)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide

Chemical Property of (1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,R_S)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,R_S)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide

There total 10 articles about (1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,R_S)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide 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%

(1R,4S)-(+)-2-exo-(<(1S,2R,4R,RS)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide (142009-87-8) + benzyl alcohol (100-51-6,185532-71-2) → (1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,RS)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide (132345-18-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 24h; Ambient temperature;

Reference yield:

(RS)-N-benzyl-3-<<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl>maleimide (132345-13-2) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2S,6R,7R)-4-Benzyl-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (132436-81-8) + (1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,RS)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide (132345-18-7)

Guidance literature:

With zinc(II) chloride; In dichloromethane; at 0 ℃; for 0.3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00006a005

Reference yield:

(1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) → (1R,4S)-(-)-N-benzyl-2-exo-(<(1S,2R,4R,RS)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulfinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboximide (132345-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 25 °C

2: 88 percent / N-chlorosuccinimide / CCl₄ / Heating

3: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / Ambient temperature

4: ZnCl₂ / CH₂Cl₂ / 1 h / 0 °C

With N-chloro-succinimide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In tetrachloromethane; dichloromethane;

upstream raw materials:

(R_S)-N-benzyl-3-<<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl>maleimide

cyclopenta-1,3-diene

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

benzyl alcohol

Downstream raw materials:

(1R,2R,6S,7S)-4-Benzyl-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

(1R,2S,6R,7S)-4-Benzyl-5-hydroxy-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

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