E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin

Base Information

• Chemical Name: E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin
• CAS No.: 671791-76-7
• Molecular Formula: C₆₃H₆₆N₄O₁₆
• Molecular Weight: 1135.23
• Mol file: 671791-76-7.mol

Synonyms:E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin

Chemical Property of E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin

There total 10 articles about E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin 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:

E/Z-1-(4-{2-[(2-aminooxyethyl)methylamino]ethoxy}phenyl)-1-(4-hydroxyphenyl)-2-phenylbutene (850256-24-5) + doxaliform (850256-41-6) → E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin (671791-76-7)

Guidance literature:

With trifluoroacetic acid; In ethanol; at 20 ℃; for 2h;

DOI:10.1021/jm030352r

Reference yield:

E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene (147323-02-2) → E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin (671791-76-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DIPEA

1.2: hydrazine

2.1: aq. TFA / ethanol

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In ethanol;

DOI:10.1021/jm049496b

Reference yield:

4-(methoxymethoxy)-4'-methoxybenzophenone (115499-97-3) → E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin (671791-76-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / n-BuLi; t-BuOK; TMEDA

2.1: 93 percent / aq. HCl

3.1: 90 percent / (n-Bu)4NHSO₄; NaOH

4.1: 57 percent / BBr₃

5.1: DIPEA

5.2: hydrazine

6.1: aq. TFA / ethanol

With hydrogenchloride; sodium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; tetra(n-butyl)ammonium hydrogensulfate; boron tribromide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In ethanol;

DOI:10.1021/jm049496b

upstream raw materials:

E/Z-1-(4-{2-[(2-aminooxyethyl)methylamino]ethoxy}phenyl)-1-(4-hydroxyphenyl)-2-phenylbutene

doxaliform

doxorubicin-5-formylsalicylamide

E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene