(1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-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

Base Information

• Chemical Name: (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-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
• CAS No.: 446063-64-5
• Molecular Formula: C₃₃H₄₇NO₆S
• Molecular Weight: 585.805

Synonyms:(1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-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

Chemical Property of (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-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

Chemical Property:

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Technology Process of (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-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

There total 6 articles about (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-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 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: 99.0%

n-butyllithium (109-72-8,29786-93-4) + (2R,6S)-4-[2-(3,4-dimethoxyphenyl)ethyl]-2-[(1S,2R,4R,SR)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methylsulfinyl]-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (446063-56-5) → (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-en-3-one (446063-64-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 6h;

DOI:10.1055/s-2002-22703

Reference yield:

(-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide (446063-58-7) → (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-en-3-one (446063-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / MCPBA / CH₂Cl₂ / 0 - 20 °C

2: CH₂Cl₂ / 0 °C

3: 99 percent / tetrahydrofuran; pentane / 6 h / -78 °C

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; pentane; 2: Diels-Alder reaction;

DOI:10.1021/jo049672o

Reference yield:

1‐(3,4‐dimethoxyphenethyl)‐1H‐pyrrole‐2,5‐dione (37597-19-6) → (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-en-3-one (446063-64-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 84 percent / NCS / CCl₄ / 16 h / Heating

3: 97 percent / MCPBA / CH₂Cl₂ / 0 - 20 °C

4: CH₂Cl₂ / 0 °C

5: 99 percent / tetrahydrofuran; pentane / 6 h / -78 °C

With N-chloro-succinimide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; tetrachloromethane; dichloromethane; pentane; 4: Diels-Alder reaction;

DOI:10.1021/jo049672o

upstream raw materials:

n-butyllithium

(2R,6S)-4-[2-(3,4-dimethoxyphenyl)ethyl]-2-[(1S,2R,4R,S_R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methylsulfinyl]-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

1‐(3,4‐dimethoxyphenethyl)‐1H‐pyrrole‐2,5‐dione

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

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