(2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol

Base Information

• Chemical Name: (2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol
• CAS No.: 143122-38-7
• Molecular Formula: C₃₆H₅₀N₆O₅S
• Molecular Weight: 678.896
• Mol file: 143122-38-7.mol

Synonyms:(2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol

Chemical Property of (2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol

There total 12 articles about (2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol 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: 73.0%

((S)-1-{(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(pyridin-2-ylsulfanyl)-butylcarbamoyl]-2-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester (143142-36-3) → (2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol (143122-38-7)

Guidance literature:

With thiophenol; triethylamine; In N,N-dimethyl-formamide; for 5h; Ambient temperature;

DOI:10.1021/jm00097a010

Reference yield:

2-Sulfanylpyridine (2637-34-5,73018-10-7) → (2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol (143122-38-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium hydride / 1.) DMF, RT, 30 min, 2.) DMF, RT, 14 h

2: 96 percent / 4N HCl / methanol; dioxane / 1 h / Ambient temperature

3: 79 percent / N-methylmorpholine (NMM), 1-hydroxybenzotriazole (HOBt), N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCl) / dimethylformamide / 14 h / Ambient temperature

4: 92 percent / 4N HCl / methanol; dioxane / 1 h / Ambient temperature

5: 73 percent / N-methylmorpholine (NMM), 1-hydroxybenzotriazole (HOBt), N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCl) / dimethylformamide / Ambient temperature

6: 73 percent / thiophenol, NEt₃ / dimethylformamide / 5 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydride; benzotriazol-1-ol; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00097a010

Reference yield:

(4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol (124577-55-5) → (2S,3S)-2-(Boc-Phe-His-amino)-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol (143122-38-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / triethylamine / CH₂Cl₂ / 6 h / Ambient temperature

2: 1.) sodium hydride / 1.) DMF, RT, 30 min, 2.) DMF, RT, 14 h

3: 96 percent / 4N HCl / methanol; dioxane / 1 h / Ambient temperature

4: 79 percent / N-methylmorpholine (NMM), 1-hydroxybenzotriazole (HOBt), N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCl) / dimethylformamide / 14 h / Ambient temperature

5: 92 percent / 4N HCl / methanol; dioxane / 1 h / Ambient temperature

6: 73 percent / N-methylmorpholine (NMM), 1-hydroxybenzotriazole (HOBt), N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCl) / dimethylformamide / Ambient temperature

7: 73 percent / thiophenol, NEt₃ / dimethylformamide / 5 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydride; benzotriazol-1-ol; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00097a010

upstream raw materials:

((S)-1-{(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(pyridin-2-ylsulfanyl)-butylcarbamoyl]-2-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

2-Sulfanylpyridine

(4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol

(4S,5S)-5-allyl-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine