1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide

Base Information

• Chemical Name: 1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide
• CAS No.: 335022-98-5
• Molecular Formula: C₂₆H₂₇N₃O₃
• Molecular Weight: 429.519
• Mol file: 335022-98-5.mol

Synonyms:1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide

Chemical Property of 1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide

There total 8 articles about 1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide 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:

β-naphthol (135-19-3) + 1-[(2S,3R)-2-benzyloxy-5-methylsulfonyloxy-3-pentyl]imidazole-4-carboxamide (294863-25-5) → 1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide (335022-98-5)

Guidance literature:

β-naphthol; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

1-[(2S,3R)-2-benzyloxy-5-methylsulfonyloxy-3-pentyl]imidazole-4-carboxamide; In N,N-dimethyl-formamide; at 60 - 70 ℃; for 6h;

DOI:10.1021/jm0499559

Reference yield:

methyl (3S,4S)-4-benzyloxy-3-(tert-butyldimethylsilyloxy)pentanoate (148409-86-3) → 1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide (335022-98-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 81.1 percent / LiAlH₄ / diethyl ether / 0.5 h

2.1: 75.5 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / cooling

3.1: 73.9 percent / imidazole / dimethylformamide / 20 °C

4.1: triethylamine / CH₂Cl₂

5.1: NaH / dimethylformamide / 20 °C

5.2: 1.98 g / dimethylformamide / 80 °C

6.1: 96.9 percent / tetrabutylammonium fluoride / tetrahydrofuran / cooling

7.1: Et₃N / CH₂Cl₂ / 1 h / cooling

8.1: potassium carbonate / dimethylformamide / 0.5 h / 20 °C

8.2: 51 mg / dimethylformamide / 6 h / 60 - 70 °C

With 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0499559

Reference yield:

(3S,4S)-4-benzyloxypentane-1,3-diol (294862-91-2) → 1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide (335022-98-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 73.9 percent / imidazole / dimethylformamide / 20 °C

2.1: triethylamine / CH₂Cl₂

3.1: NaH / dimethylformamide / 20 °C

3.2: 1.98 g / dimethylformamide / 80 °C

4.1: 96.9 percent / tetrabutylammonium fluoride / tetrahydrofuran / cooling

5.1: Et₃N / CH₂Cl₂ / 1 h / cooling

6.1: potassium carbonate / dimethylformamide / 0.5 h / 20 °C

6.2: 51 mg / dimethylformamide / 6 h / 60 - 70 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0499559

upstream raw materials:

β-naphthol

1-[(2S,3R)-2-benzyloxy-5-methylsulfonyloxy-3-pentyl]imidazole-4-carboxamide

methyl (3S,4S)-4-benzyloxy-3-(tert-butyldimethylsilyloxy)pentanoate

(3S,4S)-4-benzyloxypentane-1,3-diol