L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, pentafluorophenyl ester

Base Information

• Chemical Name: L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, pentafluorophenyl ester
• CAS No.: 17543-49-6
• Molecular Formula: C23H16F5NO4
• Molecular Weight: 465.376
• Mol file: 17543-49-6.mol

Synonyms:

Chemical Property of L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, pentafluorophenyl ester

There total 3 articles about L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, 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: 100.0%

N-Cbz-L-Phe (1161-13-3) + bis(pentafluorophenyl)sulfite (96157-57-2) → (S)-benzyloxycarbonylphenylalanine pentafluorophenyl ester (17543-49-6)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1007/BF00952635

Reference yield: 90.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + N-Cbz-L-Phe (1161-13-3) → (S)-benzyloxycarbonylphenylalanine pentafluorophenyl ester (17543-49-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)89507-7

Reference yield:

2,3,4,5,6-pentafluorophenol (771-61-9) → (S)-benzyloxycarbonylphenylalanine pentafluorophenyl ester (17543-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridine, SOCl₂ / diethyl ether / 0.5 h / 0 - 20 °C

2: 100 percent / pyridine / 20 °C

With pyridine; thionyl chloride; In diethyl ether;

DOI:10.1007/BF00952635

upstream raw materials:

2,3,4,5,6-pentafluorophenol

N-Cbz-L-Phe

bis(pentafluorophenyl)sulfite

Downstream raw materials:

(S)-2-((S)-2-benzyloxycarbonylamino-3-phenyl-propionylamino)-5-guanidinopentanoic acid

Z-L-Phe-DL-Leu-L-Val-OMe

Z-L-Phe-DL-Leu-D-Val-OMe

Z-L-Phe-L-ΔAla-L-Val-OMe

Refernces

• 1、 Il'ina,Davidovich,Rogozhin. "Bis(pentaluorophenyl) sulfite - A new reagent for the synthesis of activated pentafluorophenyl esters of N-protected amino acids". . p. 2539 - 2541. Retrieved 2007/10/02.