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
Hs Code.:

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

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

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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:

: 135-19-3
β-naphthol

: 294863-25-5
1-[(2S,3R)-2-benzyloxy-5-methylsulfonyloxy-3-pentyl]imidazole-4-carboxamide

: 335022-98-5
1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide

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:

: 148409-86-3
methyl (3S,4S)-4-benzyloxy-3-(tert-butyldimethylsilyloxy)pentanoate

: 335022-98-5
1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide

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:

: 294862-91-2
(3S,4S)-4-benzyloxypentane-1,3-diol

: 335022-98-5
1-[(2S,3R)-2-benzyloxy-5-(2-naphthyloxy)-3-pentyl]imidazole-4-carboxamide

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