14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine

Base Information

• Chemical Name: 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine
• CAS No.: 107538-88-5
• Molecular Formula: C₂₇H₂₉NO₄
• Molecular Weight: 431.532
• Mol file: 107538-88-5.mol

Synonyms:14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine

Chemical Property of 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine

There total 15 articles about 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine 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:

(S)-3,9,10-trimethoxyl-2-benzyloxytetrahydroprotoberberine → 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine (107538-88-5)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.bmc.2012.12.016

Reference yield:

3-benzyloxy-4-methoxy-β-nitrostyrene (63909-29-5,55507-05-6) → 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine (107538-88-5)

Guidance literature:

Multi-step reaction with 8 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Reflux

2: ethanol / 14 h / Reflux

3: pyridine / dichloromethane / 1.5 h / 0 - 20 °C

4: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere

5: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C

6: water; sodium hydroxide / ethanol / 3 h / 20 °C

7: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C

8: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C

With pyridine; lithium aluminium tetrahydride; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); formic acid; thionyl chloride; water; sodium hydrogencarbonate; triethylamine; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: |Bischler-Napieralski Reaction;

DOI:10.1016/j.bmc.2012.12.016

Reference yield:

3-benzyloxy-4-methoxyphenylethylamine (36455-21-7) → 14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine (107538-88-5)

Guidance literature:

Multi-step reaction with 7 steps

1: ethanol / 14 h / Reflux

2: pyridine / dichloromethane / 1.5 h / 0 - 20 °C

3: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere

4: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C

5: water; sodium hydroxide / ethanol / 3 h / 20 °C

6: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C

7: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C

With pyridine; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); formic acid; thionyl chloride; water; sodium hydrogencarbonate; triethylamine; sodium hydroxide; trichlorophosphate; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: |Bischler-Napieralski Reaction;

DOI:10.1016/j.bmc.2012.12.016

upstream raw materials:

3-benzyloxy-4-methoxy-β-nitrostyrene

(S)-(6-((6-(benzyloxy)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxyphenyl)methanol

3-benzyloxy-4-methoxyphenylethylamine

(S)-6-((6-(benzyloxy)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxylbenzyl acetate

Downstream raw materials:

corypalmine

Refernces