(1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-one

Base Information

• Chemical Name: (1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-one
• CAS No.: 187986-28-3
• Molecular Formula: C₂₂H₂₅ClO₅
• Molecular Weight: 404.891

Synonyms:(1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-one

Chemical Property of (1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-one

There total 8 articles about (1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-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:

(4R,5S,6R)-4-Dimethoxymethyl-5-isopropyl-2-methyl-6-trimethylsilanyloxy-cyclohex-2-enone (187986-23-8) → (1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.02,6]undecan-7-one (187986-28-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 79 percent / PTSA*H₂O / CHCl₃ / 6 h / Ambient temperature

2: CuI / tetrahydrofuran / -78 °C

3: Et₃N / tetrahydrofuran / -78 - 20 °C

4: 3.54 g / NaI, m-CPBA / tetrahydrofuran / 0.33 h / Ambient temperature

5: Bu₃SnH, AIBN / benzene / 1 h / Heating

6: 84 percent / TFA / benzene / 0.33 h

7: BF₃*Et₂O / CH₂Cl₂ / 3.5 h

With copper(l) iodide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; chloroform; benzene;

DOI:10.1021/ja9643432

Reference yield:

(1R,2S,5R,7R,8S)-8-Isopropyl-7-methoxy-3-methyl-2-(4-trimethylsilanyl-but-3-ynyl)-6-oxa-bicyclo[3.2.1]oct-3-en-4-ol → (1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.02,6]undecan-7-one (187986-28-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / -78 - 20 °C

2: 3.54 g / NaI, m-CPBA / tetrahydrofuran / 0.33 h / Ambient temperature

3: Bu₃SnH, AIBN / benzene / 1 h / Heating

4: 84 percent / TFA / benzene / 0.33 h

5: BF₃*Et₂O / CH₂Cl₂ / 3.5 h

With 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja9643432

Reference yield:

(1S,2S,5R,7R,8S)-3-Iodo-8-isopropyl-7-methoxy-3-methyl-2-(4-trimethylsilanyl-but-3-ynyl)-6-oxa-bicyclo[3.2.1]octan-4-one (187986-20-5) → (1S,2S,6R,8R,10R,11S)-10-(3-chloroperoxybenzoyl)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.02,6]undecan-7-one (187986-28-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Bu₃SnH, AIBN / benzene / 1 h / Heating

2: 84 percent / TFA / benzene / 0.33 h

3: BF₃*Et₂O / CH₂Cl₂ / 3.5 h

With 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; trifluoroacetic acid; In dichloromethane; benzene;

DOI:10.1021/ja9643432

upstream raw materials:

3-chloro-benzenecarboperoxoic acid

(1R,2S,6R,8R,10R,11S)-11-isopropyl-10-methoxy-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7-one

(4R,5S,6R)-4-Dimethoxymethyl-5-isopropyl-2-methyl-6-trimethylsilanyloxy-cyclohex-2-enone

(1S,2S,5R,7R,8S)-3-Iodo-8-isopropyl-7-methoxy-3-methyl-2-(4-trimethylsilanyl-but-3-ynyl)-6-oxa-bicyclo[3.2.1]octan-4-one

Downstream raw materials:

dendrobine

(1S,2S,6R,8R,11S)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7,10-dione

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