(1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 1309831-76-2
• Molecular Formula: C₃₄H₃₇NO₆S₂
• Molecular Weight: 619.803
• Mol file: 1309831-76-2.mol

Synonyms:(1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline

There total 4 articles about (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline 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: 58.0%

(S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene (1309831-72-8) + (S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide (1309831-74-0) → (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline (1309831-80-8) + (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline (1309831-76-2)

Guidance literature:

(S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; optical yield given as %de; stereoselective reaction;

DOI:10.1021/jo2007237

Reference yield:

2-(2-chloroethyl)-4,5-dimethoxybenzaldehyde (132283-68-2) → (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline (1309831-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium(IV) tetraethanolate / dichloromethane / 3 h / Reflux

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 12 h / -78 - 20 °C

With titanium(IV) tetraethanolate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo2007237

Reference yield:

1-bromo-4,5-dimethoxy-2-methylbenzene (52806-46-9) → (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-2-((S)-p-tolylsulfinyl)-1,2,3,4-tetrahydroisoquinoline (1309831-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.08 h / -78 °C

1.2: 0.33 h / -78 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 12 h / -78 - 20 °C

With tert.-butyl lithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; pentane; 1.1: Andersen synthesis / 1.2: Andersen synthesis;

DOI:10.1021/jo2007237

upstream raw materials:

(S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene

(S)-(+)-(E)-N-[2-(2-chloroethyl)-4,5-dimethoxybenzylidene]-4-methylbenzenesulfinamide

1-bromo-4,5-dimethoxy-2-methylbenzene

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

Downstream raw materials:

(1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

S-(-)-Norlaudanosine

(S)-(-)-norcoralydine