pentafluorophenyl ester of N^α-benzyloxycarbonyl-L-glutamine

Base Information

• Chemical Name: pentafluorophenyl ester of N^α-benzyloxycarbonyl-L-glutamine
• CAS No.: 17543-48-5
• Molecular Formula: C₁₉H₁₅F₅N₂O₅
• Molecular Weight: 446.331
• Mol file: 17543-48-5.mol

Synonyms:

Chemical Property of pentafluorophenyl ester of N^α-benzyloxycarbonyl-L-glutamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pentafluorophenyl ester of N^α-benzyloxycarbonyl-L-glutamine

There total 1 articles about pentafluorophenyl ester of N^α-benzyloxycarbonyl-L-glutamine 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:

2,3,4,5,6-pentafluorophenol (771-61-9) + Cbz-L-Gln (2650-64-8) → pentafluorophenyl ester of Nα-benzyloxycarbonyl-L-glutamine (17543-48-5)

Guidance literature:

With dicyclohexyl-carbodiimide;

DOI:10.1021/jo00835a086

Reference yield: 61.0%

(S)-Leu-OMe (2666-93-5) + pentafluorophenyl ester of Nα-benzyloxycarbonyl-L-glutamine (17543-48-5) → N-α-Z-L-glutaminyl-L-leucine methyl ester (33104-49-3)

Guidance literature:

In ethyl acetate; at 0 - 20 ℃; for 1.5h;

Reference yield:

pentafluorophenyl ester of Nα-benzyloxycarbonyl-L-glutamine (17543-48-5) → N-<1-(4-biphenylyl)-1-methylethoxycarbonyl>-L-leucyl-O-tert-butyl-L-tyrosyl-L-glutaminyl-L-leucine methyl ester (56867-27-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / ethyl acetate / 1.5 h / 0 - 20 °C

2: 2N HBr / acetic acid / 1 h / 20 °C

3: 73 percent / triethylamine / dimethylformamide / 1.) 1h, 0 degC, 2.) 15 min, 20 degC

4: hydrogen / palladium black / methanol / 7 h / 20 °C

5: 71.4 percent / ethyl acetate / 2.5 h / 0 - 20 °C

With hydrogen bromide; hydrogen; triethylamine; palladium; In methanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Cbz-L-Gln

Downstream raw materials:

N-^α-Z-L-glutaminyl-L-leucine methyl ester

methyl ester of N-benzyloxycarbonylglutaminyl-β-O-tert-butylasparaginylphenylalanine

N-Z-O-tert-butyl-L-tyrosyl-L-glutaminyl-L-leucine methyl ester

N-<1-(4-biphenylyl)-1-methylethoxycarbonyl>-L-leucyl-O-tert-butyl-L-tyrosyl-L-glutaminyl-L-leucine methyl ester