7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one

Base Information

• Chemical Name: 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one
• CAS No.: 154879-06-8
• Molecular Formula: C₂₇H₂₇NO₅S
• Molecular Weight: 477.581

Synonyms:7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one

Chemical Property of 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one

There total 17 articles about 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-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: 95.0%

N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide (154879-05-7) → 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one (154879-06-8)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; for 59h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81754-3

Reference yield:

O-benzylcatechol (6272-38-4) → 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one (154879-06-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 61 percent / K₂CO₃, CuO / pyridine / 20 h / Heating

2: 76 percent / 1.) LDA; 2.) HMPA / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -78 deg C, 30 min; 3.) RT, 1 h

3: 91 percent / NaIO₄ / H₂O; acetone / 15 h / Ambient temperature

4: 38 percent / trifluoroacetic anhydride (TFAA) / CH₂Cl₂ / 24 h / Ambient temperature

5: 66 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) RT, 6 h

6: 86 percent / H₂ / 5percent Pd/C / methanol / 168 h / at 6 kg/cm²

7: 92 percent / K₂CO₃ / acetone / 2 h / Heating

8: 92 percent / methanol / 5 h / 95 °C / sealed tube

9: BH₃*THF / 240 h / Heating

10: Et₃N / CH₂Cl₂ / 9 h / Ambient temperature

11: NAIO₄ / H₂O; methanol / 60 h / Ambient temperature

12: 95 percent / trifluoroacetic anhydride <(CF₃CO)2O> / CH₂Cl₂ / 59 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; borane-THF; hydrogen; tin(IV) chloride; potassium carbonate; triethylamine; trifluoroacetic anhydride; copper(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)81754-3

Reference yield:

ethyl (2-bromo-4,5-dimethoxyphenyl)acetate (91881-19-5) → 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-4-methylthio-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one (154879-06-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 61 percent / K₂CO₃, CuO / pyridine / 20 h / Heating

2: 76 percent / 1.) LDA; 2.) HMPA / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -78 deg C, 30 min; 3.) RT, 1 h

3: 91 percent / NaIO₄ / H₂O; acetone / 15 h / Ambient temperature

4: 38 percent / trifluoroacetic anhydride (TFAA) / CH₂Cl₂ / 24 h / Ambient temperature

5: 66 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) RT, 6 h

6: 86 percent / H₂ / 5percent Pd/C / methanol / 168 h / at 6 kg/cm²

7: 92 percent / K₂CO₃ / acetone / 2 h / Heating

8: 92 percent / methanol / 5 h / 95 °C / sealed tube

9: BH₃*THF / 240 h / Heating

10: Et₃N / CH₂Cl₂ / 9 h / Ambient temperature

11: NAIO₄ / H₂O; methanol / 60 h / Ambient temperature

12: 95 percent / trifluoroacetic anhydride <(CF₃CO)2O> / CH₂Cl₂ / 59 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; borane-THF; hydrogen; tin(IV) chloride; potassium carbonate; triethylamine; trifluoroacetic anhydride; copper(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)81754-3

upstream raw materials:

N-(5-benzyloxy-2,3-dimethoxyxanthen-9-ylmethyl)-N-methyl-α-(methylsulfinyl)acetamide

O-benzylcatechol

4-Bromoveratrole

ethyl (2-bromo-4,5-dimethoxyphenyl)acetate

Downstream raw materials:

7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one

7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine

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