(S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate

Base Information

• Chemical Name: (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate
• CAS No.: 886443-07-8
• Molecular Formula: C₃₈H₃₈N₂O₉
• Molecular Weight: 666.728
• Mol file: 886443-07-8.mol

Synonyms:(S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate

Chemical Property of (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate

There total 8 articles about (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate 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: 83.0%

(Z)-2-(2'-amino-4'-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene (519060-26-5) + Nα-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-serine (171778-17-9,608512-87-4) → (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate (886443-07-8)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.bmc.2016.01.007

Reference yield:

(Z)-2-(2'-nitro-4'-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene (519060-25-4) → (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate (886443-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / sodium dithionite / acetone; H₂O / 50 °C

2: 55 percent / N,N'-dicyclohexylcarbodiimide; N-hydroxybenzotriazole hydrate / dimethylformamide / 16 h / 20 °C

With sodium dithionite; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2005.12.033

Reference yield:

4-methoxy-2-nitrobenzyl bromide (57559-52-1) → (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((5-methoxy-2-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate (886443-07-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / CH₂Cl₂ / 16 h / Heating

2: 41 percent / sodium hydride / CH₂Cl₂ / 16 h / 20 °C

3: 38 percent / sodium dithionite / acetone; H₂O / 50 °C

4: 55 percent / N,N'-dicyclohexylcarbodiimide; N-hydroxybenzotriazole hydrate / dimethylformamide / 16 h / 20 °C

With sodium dithionite; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; 2: Wittig reaction;

DOI:10.1016/j.bmc.2005.12.033

upstream raw materials:

(Z)-2-(2'-amino-4'-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene

N^α-(9-fluorenylmethoxycarbonyl)-O-acetyl-L-serine

(Z)-2-(2'-nitro-4'-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene

4-methoxy-2-nitrobenzyl bromide

Refernces

• 1、 Monk, Keith A.,Siles, Rogelio,Hadimani, Mallinath B.,Mugabe, Benon E.,Ackley, J. Freeland,Studerus, Scott W.,Edvardsen, Klaus,Trawick, Mary Lynn,Garner, Charles M.,Rhodes, Monte R.,Pettit, George R.,Pinney, Kevin G.. "Design, synthesis, and biological evaluation of combretastatin nitrogen-containing derivatives as inhibitors of tubulin assembly and vascular disrupting agents". . p. 3231 - 3244. Retrieved 2007/10/03.