Enopeptin B

Base Information

• Chemical Name: Enopeptin B
• CAS No.: 139601-14-2
• Molecular Formula: C₄₆H₅₅N₇O₁₁
• Molecular Weight: 881.983
• Mol file: 139601-14-2.mol

Synonyms:

Chemical Property of Enopeptin B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Enopeptin B

There total 20 articles about Enopeptin B 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:

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) → Enopeptin B (139601-14-2)

Guidance literature:

Multi-step reaction with 7 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

4: 17 percent / HATU, Huenig base / dimethylformamide / 12 h / 0 °C

5: TFA / CH₂Cl₂ / Ambient temperature

6: N-methylmorpholine / tetrahydrofuran / 2 h / Ambient temperature

7: N-methylmorpholine / dimethylformamide / 3 h / Ambient temperature

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

DOI:10.1002/anie.199711101

Reference yield:

(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 (192068-63-6) → Enopeptin B (139601-14-2)

Guidance literature:

Multi-step reaction with 8 steps

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

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

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

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

5: 17 percent / HATU, Huenig base / dimethylformamide / 12 h / 0 °C

6: TFA / CH₂Cl₂ / Ambient temperature

7: N-methylmorpholine / tetrahydrofuran / 2 h / Ambient temperature

8: N-methylmorpholine / dimethylformamide / 3 h / Ambient temperature

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

DOI:10.1002/anie.199711101

Reference yield:

C33H47N5O11 → Enopeptin B (139601-14-2)

Guidance literature:

Multi-step reaction with 10 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

7: 17 percent / HATU, Huenig base / dimethylformamide / 12 h / 0 °C

8: TFA / CH₂Cl₂ / Ambient temperature

9: N-methylmorpholine / tetrahydrofuran / 2 h / Ambient temperature

10: N-methylmorpholine / dimethylformamide / 3 h / Ambient temperature

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

DOI:10.1002/anie.199711101

upstream raw materials:

C₄₆H₅₈N₆O₁₁

(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

C₃₁H₃₄N₂O₇

(2E,4E,6E)octa-2,4,6-triene-1,8-dial