(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

Base Information

• Chemical Name: (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
• CAS No.: 132374-47-1
• Molecular Formula: C₂₆H₃₃NO₄S
• Molecular Weight: 455.618

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 94.0%

(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) → (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[5.2.1.02,6]dec-8-en-3-one (132374-47-1)

Guidance literature:

With sodium tetrahydroborate;

DOI:10.1021/jo00006a005

Reference yield:

1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) → (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[5.2.1.02,6]dec-8-en-3-one (132374-47-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Et₃N / benzene / 6 h / Ambient temperature

2: 88 percent / N-chlorosuccinimide / CCl₄ / 6 h / Heating

3: 98 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / -80 deg C to r.t.

4: ZnCl₂ / CH₂Cl₂ / 0.3 h / 0 °C

5: 94 percent / NaBH₄

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

DOI:10.1021/jo00006a005

Reference yield:

(1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) → (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[5.2.1.02,6]dec-8-en-3-one (132374-47-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Et₃N / benzene / 6 h / Ambient temperature

2: 88 percent / N-chlorosuccinimide / CCl₄ / 6 h / Heating

3: 98 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / -80 deg C to r.t.

4: ZnCl₂ / CH₂Cl₂ / 0.3 h / 0 °C

5: 94 percent / NaBH₄

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

DOI:10.1021/jo00006a005

upstream raw materials:

(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

1-benzyl-1H-pyrrole-2,5-dione

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

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

Downstream raw materials:

(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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