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

Base Information

• Chemical Name: (-)-(1R,R_S)-2-benzyl 3-methyl 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate
• CAS No.: 121611-75-4
• Molecular Formula: C₂₇H₃₄O₆S
• Molecular Weight: 486.629
• Mol file: 121611-75-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (-)-(1R,R_S)-2-benzyl 3-methyl 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-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: 86.0%

benzyl bromide (100-39-0) + (+)-(1R,RS)-3-methyl hydrogen 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate (121611-74-3) → (-)-(1R,RS)-2-benzyl 3-methyl 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate (121611-75-4)

Guidance literature:

With 18-crown-6 ether; sodium hydride; In acetonitrile; at 50 ℃; for 12h;

DOI:10.1016/S0040-4039(00)82289-3

Reference yield:

(1R,2R,3S,4S)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester (121611-73-2) → (-)-(1R,RS)-2-benzyl 3-methyl 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate (121611-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / AlBr₃, Me₂S / CH₂Cl₂ / 4 h / -20 °C

2: 86 percent / NaH / 18-crown-6 / acetonitrile; diethyl ether / 12 h / 50 °C

With aluminum tri-bromide; dimethylsulfide; sodium hydride; 18-crown-6 ether; In diethyl ether; dichloromethane; acetonitrile;

Reference yield:

(1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) → (-)-(1R,RS)-2-benzyl 3-methyl 2-exo-(<(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl>methylsulphinyl)bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-dicarboxylate (121611-75-4)

Guidance literature:

Multi-step reaction with 5 steps

1: diphenylmethylphosphine / acetonitrile / 12 h / Ambient temperature; E/Z ratio 4:1

2: 70 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 0 °C

3: 68 percent / CH₂Cl₂ / 2.5 h / -20 °C / cat. ZnCl₂

4: 100 percent / AlBr₃, Me₂S / CH₂Cl₂ / 4 h / 0 °C

5: 86 percent / NaH, 18-crown-6 / acetonitrile / 12 h / 50 °C

With aluminum tri-bromide; di-phenyl-methyl-phosphine; 18-crown-6 ether; dimethylsulfide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)82289-3

upstream raw materials:

benzyl bromide

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

(1R,2R,3S,4S)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester

(1S,2R,4R)-(-)-10-mercaptoisoboneol

Downstream raw materials:

(-)-(1R,4S)-2-Benzyl 3-methyl bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarboxylate