(E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl ester

Base Information

• Chemical Name: (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl ester
• CAS No.: 186020-77-9
• Molecular Formula: C₄₂H₅₀N₂O₁₂
• Molecular Weight: 774.865
• Mol file: 186020-77-9.mol

Synonyms:

Chemical Property of (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl ester

There total 5 articles about (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl 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:

(E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid tert-butyl ester (166668-33-3) → (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl ester (186020-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / Bu₄NBr, aq. NaHCO₃ / CH₂Cl₂

2: 84 percent / TFA / 0.75 h

3: 1.) DCC, HONSu, 2.) DIEA / 1.) CH₂Cl₂, 25 min, 2.) AcOEt, 17 h

With 1-hydroxy-pyrrolidine-2,5-dione; tetrabutylammomium bromide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo960743w

Reference yield:

3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (186020-66-6,892154-71-1) → (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl ester (186020-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / NaOH, Bu₄NHSO₄ / H₂O; CH₂Cl₂ / 0.75 h

2: 72 percent / Bu₄NBr, aq. NaHCO₃ / CH₂Cl₂

3: 84 percent / TFA / 0.75 h

4: 1.) DCC, HONSu, 2.) DIEA / 1.) CH₂Cl₂, 25 min, 2.) AcOEt, 17 h

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; tetrabutylammomium bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; water;

DOI:10.1021/jo960743w

Reference yield:

2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine phenacyl ester (186020-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / Na / tetrahydrofuran / 20 h

2: 45 percent / NaOH, Bu₄NHSO₄ / H₂O; CH₂Cl₂ / 0.75 h

3: 72 percent / Bu₄NBr, aq. NaHCO₃ / CH₂Cl₂

4: 84 percent / TFA / 0.75 h

5: 1.) DCC, HONSu, 2.) DIEA / 1.) CH₂Cl₂, 25 min, 2.) AcOEt, 17 h

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; tetrabutylammomium bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo960743w

upstream raw materials:

(E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid

(E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid tert-butyl ester

3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

(E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid tert-butyl ester