14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine

Base Information

• Chemical Name: 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine
• CAS No.: 1429118-98-8
• Molecular Formula: C₂₆H₂₅NO₄
• Molecular Weight: 415.489
• Mol file: 1429118-98-8.mol

Synonyms:14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine

Chemical Property of 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine

There total 15 articles about 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine 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:

C26H26ClNO4 → 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine (1429118-98-8)

Guidance literature:

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

DOI:10.1016/j.bmc.2012.12.016

Reference yield:

3,4-methylenedioxyphenylethylamine (1484-85-1) → 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine (1429118-98-8)

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: formic acid; triethylamine; Noyori's catalyst / 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; Noyori's catalyst; 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

Reference yield:

Methyl 4-hydroxyphenylacetate (14199-15-6) → 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine (1429118-98-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: acetic acid; bromine / 2 h / 20 °C

2.1: potassium carbonate / acetone / Reflux

3.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / Inert atmosphere; Microwave irradiation

4.1: phenylboronic acid / toluene / 1 h / Reflux; Dean-Stark

4.2: 46 h / 100 °C / Molecular sieve; Sealed tube

4.3: 2 h / Reflux

5.1: potassium carbonate / acetone / 4 h / Reflux

6.1: ethanol / 14 h / Reflux

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

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

9.1: formic acid; triethylamine; Noyori's catalyst / N,N-dimethyl-formamide / 20 °C

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

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

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

With pyridine; Noyori's catalyst; formic acid; thionyl chloride; water; bromine; copper; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; copper(II) oxide; potassium hydroxide; sodium hydroxide; trichlorophosphate; phenylboronic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 8.1: |Bischler-Napieralski Reaction;

DOI:10.1016/j.bmc.2012.12.016

upstream raw materials:

3,4-methylenedioxyphenylethylamine

Methyl 4-hydroxyphenylacetate

methyl 3-bromo-4-hydroxyphenylacetate

methyl 2-(3-bromo-4-methoxyphenyl)acetate

Downstream raw materials:

5,6,13,14-tetrahydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine