(S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-yl)-propionamide

Base Information

• Chemical Name: (S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-yl)-propionamide
• CAS No.: 192068-67-0
• Molecular Formula: C₂₉H₄₀N₆O₇
• Molecular Weight: 584.673

Synonyms:(S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-yl)-propionamide

Chemical Property of (S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-yl)-propionamide

Chemical Property:

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Technology Process of (S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-yl)-propionamide

There total 11 articles about (S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-yl)-propionamide 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: 100.0%

C37H46N6O9 → (S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.07,11]docos-3-yl)-propionamide (192068-67-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 42h; under 760.051 Torr;

DOI:10.1021/np500158q

Reference yield:

C33H47N5O11 → (S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.07,11]docos-3-yl)-propionamide (192068-67-0)

Guidance literature:

Multi-step reaction with 6 steps

1: EDC / CH₂Cl₂ / 20 h

2: HCl / dioxane / 2 h / Ambient temperature

3: aq. NaHCO₃ / CHCl₃ / 6 h / Ambient temperature

4: H₂, HCl / Pd/C / methanol / 6 h / Ambient temperature

5: HATU, Huenig base / dimethylformamide / 12 h / 0 °C

6: HBr / acetic acid / 0.5 h / Ambient temperature

With hydrogenchloride; hydrogen bromide; hydrogen; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/anie.199711101

Reference yield:

benzyl ((6S,9S,11aS,17S,20aS)-6,9,10-trimethyl-5,8,11,16,20-pentaoxohexadecahydro-1H,5H,16Hdipyrrolo[2,1-c:2',1'-l][1]oxa[4,7,10,13]tetraazacyclohexadecin-17-yl)carbamate (192068-64-7) → (S)-2-Amino-3-phenyl-N-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.07,11]docos-3-yl)-propionamide (192068-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, HCl / Pd/C / methanol / 6 h / Ambient temperature

2: HATU, Huenig base / dimethylformamide / 12 h / 0 °C

3: HBr / acetic acid / 0.5 h / Ambient temperature

With hydrogenchloride; hydrogen bromide; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/anie.199711101

upstream raw materials:

[(S)-2-Phenyl-1-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

(3S,7S,13S,16S,19S)-3-Amino-13,16,17-trimethyl-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docosane-2,6,12,15,18-pentaone

benzyl ((6S,9S,11aS,17S,20aS)-6,9,10-trimethyl-5,8,11,16,20-pentaoxohexadecahydro-1H,5H,16Hdipyrrolo[2,1-c:2',1'-l][1]oxa[4,7,10,13]tetraazacyclohexadecin-17-yl)carbamate

(S)-1-((S)-2-{(S)-2-[Methyl-((S)-pyrrolidine-2-carbonyl)-amino]-propionylamino}-propionyl)-pyrrolidine-2-carboxylic acid (S)-2-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonyl-ethyl ester

Downstream raw materials:

(2E,4E,6E,8E,10E)-11-[(S)-2-Phenyl-1-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-ylcarbamoyl)-ethylcarbamoyl]-undeca-2,4,6,8,10-pentaenoic acid tert-butyl ester

Enopeptin B

(2E,4E,6E,8E,10E)-11-[(S)-2-Phenyl-1-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.0^7,11]docos-3-ylcarbamoyl)-ethylcarbamoyl]-undeca-2,4,6,8,10-pentaenoic acid

C₄₆H₅₈N₆O₁₁

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