{(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 1053747-26-4
• Molecular Formula: C₂₃H₃₉N₃O₄S₃
• Molecular Weight: 517.778

Synonyms:

Chemical Property of {(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester

There total 7 articles about {(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester 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:

(4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol (124577-55-5) → {(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester (1053747-26-4)

Guidance literature:

Multi-step reaction with 4 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: 4N HCl / dioxane; methanol / 1 h / Ambient temperature

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

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

DOI:10.1021/jm00097a010

Reference yield:

(4S,5S)-5-allyl-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine (143122-11-6) → {(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester (1053747-26-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) ozone, 2.) Me₂S / 1.) GH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, overnight

2: sodium borohydride / methanol / 3 h / 0 °C

3: 86 percent / triethylamine / CH₂Cl₂ / 6 h / Ambient temperature

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

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

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

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

DOI:10.1021/jm00097a010

Reference yield:

(4S,5S)-3-(tert-butoxycarbonyl)-4-cyclohexylmethyl-5-formylmethyl-2,2-dimethyl-1,3-oxazolidine (145341-80-6) → {(R)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethyl}-carbamic acid tert-butyl ester (1053747-26-4)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium borohydride / methanol / 3 h / 0 °C

2: 86 percent / triethylamine / CH₂Cl₂ / 6 h / Ambient temperature

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

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

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

With 4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; sodium hydride; benzotriazol-1-ol; 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:

N-(tert-butoxycarbonyl)-S-methyl-L-cysteine

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

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

(4S,5S)-3-(tert-butoxycarbonyl)-4-cyclohexylmethyl-5-formylmethyl-2,2-dimethyl-1,3-oxazolidine

Downstream raw materials:

(2S,3S)-2-<<(2S)-2-<<(4-aminopiperidino)carbonyl>oxy>-3-phenylpropionyl>-Cys(Me)-amino>-1-cyclohexyl-5-(2-thiazolylthio)-3-pentanol bis(trifluoroacetate)

4-tert-Butoxycarbonylamino-piperidine-1-carboxylic acid (S)-1-{(R)-1-[(1S,2S)-1-cyclohexylmethyl-2-hydroxy-4-(thiazol-2-ylsulfanyl)-butylcarbamoyl]-2-methylsulfanyl-ethylcarbamoyl}-2-phenyl-ethyl ester

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