1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

Base Information

• Chemical Name: 1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol
• CAS No.: 247174-16-9
• Molecular Formula: C₄₂H₄₆N₂O₂Si
• Molecular Weight: 638.925
• Mol file: 247174-16-9.mol

Synonyms:1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

Chemical Property of 1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

There total 2 articles about 1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 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: 92.0%

(6-bromonaphthalen-2-yloxy)-tert-butyldimethylsilane (100751-65-3) + 2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanone → 1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (247174-16-9)

Guidance literature:

(6-bromonaphthalen-2-yloxy)-tert-butyldimethylsilane; With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 0.333333h;

2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanone; In tetrahydrofuran; at -70 ℃; for 0.833333h;

With water; In tetrahydrofuran;

DOI:10.1016/j.bmc.2011.01.017

Reference yield:

6-bromo-naphthalen-2-ol (15231-91-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (247174-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C

1.2: 0 °C

2.1: n-butyllithium / tetrahydrofuran / 0.33 h / -70 °C

2.2: 0.83 h / -70 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.01.017

Reference yield:

1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (247174-16-9) → 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-propyl-2-naphthamide (337522-47-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: pyridine / 1 h / 0 °C

3.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 14 h / 70 °C / 760.05 Torr

4.1: methanol; sodium hydroxide / tetrahydrofuran / 2 h / 60 °C

4.2: 0 °C

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C

With pyridine; methanol; 1,1'-bis-(diphenylphosphino)ferrocene; tetrabutyl ammonium fluoride; palladium diacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.01.017

upstream raw materials:

6-bromo-naphthalen-2-ol

tert-butyldimethylsilyl chloride

(6-bromonaphthalen-2-yloxy)-tert-butyldimethylsilane

Downstream raw materials:

6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl trifluoromethanesulfonate

6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthamide

6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-2-naphthamide

N-ethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthamide