benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

Base Information

• Chemical Name: benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate
• CAS No.: 1310875-40-1
• Molecular Formula: C₃₃H₅₄N₂O₅Si₂
• Molecular Weight: 614.973

Synonyms:benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

Chemical Property of benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

There total 3 articles about benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate 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: 91.0%

benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate (1310875-39-8) + tert-butyldimethylsilyl chloride (18162-48-6) → benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate (1310875-40-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jo200758r

Reference yield:

N-benzyloxycarbonylglycinal (67561-03-9) → benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate (1310875-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / dichloromethane; 2,2,2-trifluoroethanol / 10 h / 0 °C / Inert atmosphere; Molecular sieve

2: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

With 1H-imidazole; acetic acid; In dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide; 1: Pictet-Spengler cyclisation;

DOI:10.1021/jo200758r

Reference yield:

(S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol (686776-27-2) → benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate (1310875-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / dichloromethane; 2,2,2-trifluoroethanol / 10 h / 0 °C / Inert atmosphere; Molecular sieve

2: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

With 1H-imidazole; acetic acid; In dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide; 1: Pictet-Spengler cyclisation;

DOI:10.1021/jo200758r

upstream raw materials:

benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

tert-butyldimethylsilyl chloride

N-benzyloxycarbonylglycinal

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

Downstream raw materials:

C₅₅H₈₈BrN₃O₁₀Si₃

C₃₇H₄₄BrN₃O₁₀

C₄₉H₇₄BrN₃O₁₀Si₂

C₄₉H₇₂BrN₃O₁₀Si₂

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