(S)-9-hydroxy-1,2,3-trimethoxyberbine

Base Information

• Chemical Name: (S)-9-hydroxy-1,2,3-trimethoxyberbine
• CAS No.: 1316259-14-9
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• Mol file: 1316259-14-9.mol

Synonyms:

Chemical Property of (S)-9-hydroxy-1,2,3-trimethoxyberbine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-9-hydroxy-1,2,3-trimethoxyberbine

There total 10 articles about (S)-9-hydroxy-1,2,3-trimethoxyberbine 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: 39.0%

1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1277187-96-8) → (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1316259-15-0) + (S)-9-hydroxy-1,2,3-trimethoxyberbine (1316259-14-9)

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:

1-(3-benzyloxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1277187-95-7) → (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1316259-15-0) + (S)-9-hydroxy-1,2,3-trimethoxyberbine (1316259-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen; acetic acid / methanol / 16 h

2: berberine bridge enzyme; tris hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction

With berberine bridge enzyme; palladium 10% on activated carbon; hydrogen; tris hydrochloride; acetic acid; magnesium chloride; In methanol; toluene;

DOI:10.1021/jo201056f

Reference yield:

2-(3-benzyloxyphenyl)-N-methyl-N-(3,4,5-trimethoxyphenethyl)acetamide (1277187-94-6) → (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1316259-15-0) + (S)-9-hydroxy-1,2,3-trimethoxyberbine (1316259-14-9)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 20 °C / Inert atmosphere; Cooling with ice

2.1: palladium 10% on activated carbon; hydrogen; acetic acid / methanol / 16 h

3.1: berberine bridge enzyme; tris hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction

With berberine bridge enzyme; palladium 10% on activated carbon; hydrogen; tris hydrochloride; acetic acid; magnesium chloride; trichlorophosphate; In methanol; toluene; acetonitrile; 1.1: Bischler-Napieralski cyclization;

DOI:10.1021/jo201056f

upstream raw materials:

2-(3-benzyloxyphenyl)-N-methyl-N-(3,4,5-trimethoxyphenethyl)acetamide

1-(3-benzyloxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

m-hydroxyphenylacetic acid

Refernces