Phenol,3-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-

Base Information

• Chemical Name: Phenol,3-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-
• CAS No.: 151841-47-3
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• Mol file: 151841-47-3.mol

Synonyms:Phenol,3-[(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl]-, (R)-;(+)-Anicanine; Anicanine

Chemical Property of Phenol,3-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenol,3-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-

There total 14 articles about Phenol,3-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]- 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: 50.0%

rac-1-(3-hydroxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1718-82-7) → (R)-6,7-dimethoxy-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline (151841-47-3) + (S)-2,3-dimethoxy-9-hydroxyberbine (1316258-58-8) + 2,3-dimethoxy-11-hydroxyberbine (19779-86-3)

Guidance literature:

With berberine bridge enzyme; tris hydrochloride; magnesium chloride; catalase; In toluene; at 40 ℃; for 24h; pH=9; optical yield given as %ee; enantioselective reaction; Darkness; aq. buffer; Inert atmosphere; Enzymatic reaction;

DOI:10.1002/anie.201006268

Reference yield: 42.0%

rac-1-(3-hydroxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1718-82-7) → (R)-6,7-dimethoxy-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline (151841-47-3) + (S)-2,3-dimethoxy-9-hydroxyberbine (1316258-58-8)

Guidance literature:

With berberine bridge enzyme; tris hydrochloride; magnesium chloride; In toluene; at 40 ℃; for 24h; pH=9; optical yield given as %ee; enantioselective reaction; Darkness; Enzymatic reaction;

DOI:10.1021/jo201056f

Reference yield:

rac-1-(3-hydroxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1718-82-7) → S-Armepavine (1718-82-7) + (R)-6,7-dimethoxy-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline (151841-47-3)

Guidance literature:

With recombinant monoamine oxidase D₁₁ from Aspergillus niger; In aq. phosphate buffer; dimethyl sulfoxide; at 37 ℃; for 24h; pH=7.7; Reagent/catalyst; Time; Resolution of racemate; Enzymatic reaction;

DOI:10.1039/c4cy00642a

upstream raw materials:

2-(3-benzyloxyphenyl)-N-(3,4-dimethoxyphenethyl)-N-methylacetamide

m-hydroxyphenylacetic acid

3-benzyloxyphenylacetic acid

rac-1-(3-hydroxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline