(1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone

Base Information

• Chemical Name: (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone
• CAS No.: 1428470-94-3
• Molecular Formula: C₂₅H₂₈O₈
• Molecular Weight: 456.493
• Mol file: 1428470-94-3.mol

Synonyms:(1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone

Chemical Property of (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone

There total 10 articles about (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone 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: 92.0%

(1R,2R)-2-(tert-butoxylcarbonyl)-4-hydroxy-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene → (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone (1428470-94-3)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo400147f

Reference yield:

Sesamol (533-31-3) → (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone (1428470-94-3)

Guidance literature:

Multi-step reaction with 9 steps

1: zinc trifluoromethanesulfonate / dichloromethane / 9 h / 30 °C

2: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; water / 1 h / 20 °C

3: pyridine / dichloromethane / -40 - 0 °C

4: lithium chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 7 h / 50 °C

5: N-iodo-succinimide / tetrahydrofuran; water / 7 h / 20 °C

6: 2,6-dimethylpyridine / dichloromethane / 8 h / 20 °C

7: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 10 h / -78 °C

8: tetrabutyl ammonium fluoride / tetrahydrofuran / 8 h / 20 °C

9: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; samarium diiodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tetrabutyl ammonium fluoride; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 4: |Stille Cross Coupling;

DOI:10.1021/jo400147f

Reference yield:

(R)-tert-butyl 3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate (1428470-86-3) → (1R,2R)-2-(tert-butoxylcarbonyl)-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2,3-dihydro-4(1H)-naphthalenone (1428470-94-3)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / dichloromethane / -40 - 0 °C

2: lithium chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 7 h / 50 °C

3: N-iodo-succinimide / tetrahydrofuran; water / 7 h / 20 °C

4: 2,6-dimethylpyridine / dichloromethane / 8 h / 20 °C

5: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 10 h / -78 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 8 h / 20 °C

7: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 2: |Stille Cross Coupling;

DOI:10.1021/jo400147f

upstream raw materials:

Sesamol

(2S,3R)-tert-butyl 2-benzylamino-3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate

(R)-tert-butyl 3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate

(R)-tert-butyl 3-[4,5-methylenedioxy-2-(trifluoromethanesulfonyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propanoate

Downstream raw materials:

(-)-3-(hydroxymethyl)picropodophyllone