(1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol

Base Information

• Chemical Name: (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol
• CAS No.: 1218781-84-0
• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.423

Synonyms:(1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol

Chemical Property of (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol

Chemical Property:

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Technology Process of (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol

There total 4 articles about (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol 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: 89.0%

benzyloxyacetoaldehyde (60656-87-3) + (S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol (686776-27-2) → (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol (1218781-84-0) + (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-6-methyl-1,2,3,4-tetra-hydroisoquinolin-8-ol (1218781-83-9)

Guidance literature:

With acetic acid; In dichloromethane; 2,2,2-trifluoroethanol; at -10 - 0 ℃; for 10h; regioselective reaction; Molecular sieve;

DOI:10.1021/np400538q

Reference yield:

Z-L-Tyr-OH (1164-16-5) → (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol (1218781-84-0) + (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-6-methyl-1,2,3,4-tetra-hydroisoquinolin-8-ol (1218781-83-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: borax; sodium hydroxide / water / 0.5 h / 25 °C / Inert atmosphere

1.2: 24 h / 40 °C / Inert atmosphere

2.1: Dichloromethyl methyl ether; titanium tetrachloride / dichloromethane / 1.5 h / -30 - 25 °C / Inert atmosphere

2.2: 25 °C / Inert atmosphere

2.3: 2 h / 25 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 25 °C / 760.05 Torr

4.1: acetic acid / dichloromethane; 2,2,2-trifluoroethanol / 4 h / -10 - 2 °C / Inert atmosphere; Molecular sieve

With borax; Dichloromethyl methyl ether; palladium 10% on activated carbon; hydrogen; titanium tetrachloride; acetic acid; sodium hydroxide; In methanol; dichloromethane; 2,2,2-trifluoroethanol; water; 4.1: |Pictet-Spengler Synthesis;

DOI:10.1002/anie.201900035

Reference yield:

N-benzyloxycarbonyl-3-methyl-4-methoxy-L-phenylalanine methyl ester (1199794-65-4) → (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-8-methyl-1,2,3,4-tetra-hydroisoquinolin-6-ol (1218781-84-0) + (1R,3S)-1-(benzyloxymethyl)-3-(hydroxyl-methyl)-7-methoxy-6-methyl-1,2,3,4-tetra-hydroisoquinolin-8-ol (1218781-83-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dichloromethyl methyl ether; titanium tetrachloride / dichloromethane / 1.5 h / -30 - 25 °C / Inert atmosphere

1.2: 25 °C / Inert atmosphere

1.3: 2 h / 25 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 25 °C / 760.05 Torr

3.1: acetic acid / dichloromethane; 2,2,2-trifluoroethanol / 4 h / -10 - 2 °C / Inert atmosphere; Molecular sieve

With Dichloromethyl methyl ether; palladium 10% on activated carbon; hydrogen; titanium tetrachloride; acetic acid; In methanol; dichloromethane; 2,2,2-trifluoroethanol; 3.1: |Pictet-Spengler Synthesis;

DOI:10.1002/anie.201900035

upstream raw materials:

benzyloxyacetoaldehyde

(S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol

N-benzyloxycarbonyl-3-hydroxy-4-methoxy-5-methyl-L-phenylalaninol

Z-L-Tyr-OH

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