2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl ester

Base Information

• Chemical Name: 2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl ester
• CAS No.: 511257-19-5
• Molecular Formula: C₆₁H₅₂Br₄F₅N₅O₁₃
• Molecular Weight: 1477.72

Synonyms:

Chemical Property of 2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl ester

There total 23 articles about 2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl 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:

3,4-dihydroxybenzaldehyde (139-85-5) → 2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl ester (511257-19-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 92 percent / Br₂ / acetic acid

2: Li₂CO₃ / dimethylformamide / 4 h

3: K₂CO₃ / 2 h

4: 82 percent / NaHMDS / 0.5 h / -78 - 20 °C

5: HF-pyr / 10 h / 20 °C

6: 76 percent / RhCl₃*3H₂O / ethanol / 12 h / Heating

7: 91 percent / K₂CO₃ / dimethylformamide / 4 h

8: LiOH / tetrahydrofuran; methanol; H₂O

9: K₂CO₃

10: NaHMDS / 0.5 h / -78 - 20 °C

11: HF-pyr / 10 h / 20 °C

12: 90 percent / Et₃N; PPh₃; HCO₂H / Pd(OAc)2 / tetrahydrofuran / 3 h

13: 78 percent / DCC; HOBT / CH₂Cl₂ / 10 h

14: LiOH / tetrahydrofuran; methanol; H₂O

15: DCC / CH₂Cl₂ / 10 h

With pyridine; lithium hydroxide; rhodium(III) chloride; formic acid; hydrogen fluoride; bromine; sodium hexamethyldisilazane; lithium carbonate; potassium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02378-X

Reference yield:

3-bromo-4-methoxy-5-hydroxybenzaldehyde (23354-30-5) → 2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl ester (511257-19-5)

Guidance literature:

Multi-step reaction with 13 steps

1: K₂CO₃ / 2 h

2: 82 percent / NaHMDS / 0.5 h / -78 - 20 °C

3: HF-pyr / 10 h / 20 °C

4: 76 percent / RhCl₃*3H₂O / ethanol / 12 h / Heating

5: 91 percent / K₂CO₃ / dimethylformamide / 4 h

6: LiOH / tetrahydrofuran; methanol; H₂O

7: K₂CO₃

8: NaHMDS / 0.5 h / -78 - 20 °C

9: HF-pyr / 10 h / 20 °C

10: 90 percent / Et₃N; PPh₃; HCO₂H / Pd(OAc)2 / tetrahydrofuran / 3 h

11: 78 percent / DCC; HOBT / CH₂Cl₂ / 10 h

12: LiOH / tetrahydrofuran; methanol; H₂O

13: DCC / CH₂Cl₂ / 10 h

With pyridine; lithium hydroxide; rhodium(III) chloride; formic acid; hydrogen fluoride; sodium hexamethyldisilazane; potassium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02378-X

Reference yield:

3-allyloxy-5-bromo-4-methoxy-benzaldehyde (511257-05-9) → 2-benzyloxyimino-3-(4-{5-[2-benzyloxyimino-2-(2-{3-bromo-4-[3-bromo-5-(2-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-phenyl}-ethylcarbamoyl)-ethyl]-3-bromo-2-methoxy-phenoxy}-5-bromo-2-nitro-phenyl)-propionic acid pentafluorophenyl ester (511257-19-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 82 percent / NaHMDS / 0.5 h / -78 - 20 °C

2: HF-pyr / 10 h / 20 °C

3: 76 percent / RhCl₃*3H₂O / ethanol / 12 h / Heating

4: 91 percent / K₂CO₃ / dimethylformamide / 4 h

5: LiOH / tetrahydrofuran; methanol; H₂O

6: K₂CO₃

7: NaHMDS / 0.5 h / -78 - 20 °C

8: HF-pyr / 10 h / 20 °C

9: 90 percent / Et₃N; PPh₃; HCO₂H / Pd(OAc)2 / tetrahydrofuran / 3 h

10: 78 percent / DCC; HOBT / CH₂Cl₂ / 10 h

11: LiOH / tetrahydrofuran; methanol; H₂O

12: DCC / CH₂Cl₂ / 10 h

With pyridine; lithium hydroxide; rhodium(III) chloride; formic acid; hydrogen fluoride; sodium hexamethyldisilazane; potassium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02378-X

upstream raw materials:

2,3,4,5,6-pentafluorophenol

3-bromo-4-methoxy-5-hydroxybenzaldehyde

3,4-dihydroxybenzaldehyde

3-allyloxy-5-bromo-4-methoxy-benzaldehyde

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