N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine

Base Information

• Chemical Name: N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine
• CAS No.: 150577-71-2
• Molecular Formula: C₂₉H₃₇N₇O₇
• Molecular Weight: 595.655

Synonyms:N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine

Chemical Property of N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine

Chemical Property:

Purity/Quality:

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Technology Process of N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine

There total 5 articles about N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine 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: 95.3%

N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine (129765-76-0) → N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine (150577-71-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jm00071a009

Reference yield:

(4S,5R)-3-(tert-butyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-<(1S)-3-(2-pyridyl)-1-hydroxypropyl>oxazolidine → N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine (150577-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) TFA, 2.) aq. TFA / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 3 h

2: 65.3 percent / HOBt*H₂O, HBTU, N-ethylmorpholine / dimethylformamide / 24 h / Ambient temperature

3: 95.3 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

With N-ethylmorpholine;; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00071a009

Reference yield:

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexane (150577-70-1) → N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine (150577-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65.3 percent / HOBt*H₂O, HBTU, N-ethylmorpholine / dimethylformamide / 24 h / Ambient temperature

2: 95.3 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

With N-ethylmorpholine;; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00071a009

upstream raw materials:

N-im-(2,4-dinitrophenyl)-L-histidyl>-(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexane

Boc-His(Dnp)-OH

Downstream raw materials:

Methyl-{2-[methyl-(morpholine-4-carbonyl)-amino]-ethyl}-carbamic acid (S)-1-{(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-pyridin-2-yl-pentylcarbamoyl)-2-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2-phenyl-ethyl ester

4-tert-Butoxycarbonylamino-piperidine-1-carboxylic acid (S)-1-{(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-pyridin-2-yl-pentylcarbamoyl)-2-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2-phenyl-ethyl ester

N--(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6(2-pyridyl)-hexane-2-amide acetate

(1-{(S)-2-[(S)-1-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-pyridin-2-yl-pentylcarbamoyl)-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-3-phenyl-propane-1-sulfonyl}-piperidin-4-yl)-carbamic acid tert-butyl ester

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