[(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

Base Information

Chemical Name:[(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester
CAS No.:105852-63-9
Molecular Formula:C₃₃H₅₁N₅O₅
Molecular Weight:597.798
Hs Code.:

Synonyms:[(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

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Chemical Property of [(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

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Technology Process of [(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

There total 8 articles about [(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl 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:

: 556-24-1
methyl 3-methylbutanoate

: 105852-63-9
[(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / diisopropylamine, n-butyllitium / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / Ambient temperature

2: 42 percent / potassium tert-butoxide, H₂O / diethyl ether / 18 h / Ambient temperature

3: 1.) hydroxybenzotriazole, dicyclohexylcarbodiimide / 1.) DMF, 0 deg C, 3 d, 2.) 0 deg C, 2 h; room temperature, 24 h

4: 99 percent / hydrogen / 10percent Pd-C / methanol; H₂O / 4 h / 25 °C

5: 1.) N-hydroxynorbornane-exo-2,3-dicarboximide, dicyclohexylcarbodiimide, 2.) 50percent aq. acetic acid / 1.) DMF, room temperature, 16 h, 2.) 25 deg C, 1 h

With n-butyllithium; potassium tert-butylate; water; hydrogen; benzotriazol-1-ol; acetic acid; diisopropylamine; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water;
DOI:10.1021/jm00117a027

Reference yield:

: 105852-50-4
3-(benzyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-(iodomethyl)-(4S,5R)-1,3-oxazolidine

: 105852-63-9
[(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / diisopropylamine, n-butyllitium / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / Ambient temperature

2: 42 percent / potassium tert-butoxide, H₂O / diethyl ether / 18 h / Ambient temperature

3: 1.) hydroxybenzotriazole, dicyclohexylcarbodiimide / 1.) DMF, 0 deg C, 3 d, 2.) 0 deg C, 2 h; room temperature, 24 h

4: 99 percent / hydrogen / 10percent Pd-C / methanol; H₂O / 4 h / 25 °C

5: 1.) N-hydroxynorbornane-exo-2,3-dicarboximide, dicyclohexylcarbodiimide, 2.) 50percent aq. acetic acid / 1.) DMF, room temperature, 16 h, 2.) 25 deg C, 1 h

With n-butyllithium; potassium tert-butylate; water; hydrogen; benzotriazol-1-ol; acetic acid; diisopropylamine; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water;
DOI:10.1021/jm00117a027

Reference yield:

: 105852-65-1
(2S)-2-[(4S,5S)-3-benzyloxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl]methyl-N-butyl-3-methylbutanamide

: 105852-63-9
[(S)-1-((1S,2S,4S)-4-Butylcarbamoyl-1-cyclohexylmethyl-2-hydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / hydrogen / 10percent Pd-C / methanol; H₂O / 4 h / 25 °C

2: 1.) N-hydroxynorbornane-exo-2,3-dicarboximide, dicyclohexylcarbodiimide, 2.) 50percent aq. acetic acid / 1.) DMF, room temperature, 16 h, 2.) 25 deg C, 1 h

With hydrogen; acetic acid; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); palladium on activated charcoal; In methanol; water;
DOI:10.1021/jm00117a027