206060-40-4

Basic information

• Product Name: FMOC-L-3-METHOXYPHENYLALANINE
• Synonyms: (S)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-(3-METHOXY-PHENYL)-PROPIONIC ACID;(S)-N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-3-METHOXY-PHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-(3-METHOXY)PHENYLALANINE;FMOC-PHE(3-OME)-OH;FMOC-S-PHE(3-OME)-OH;Fmoc-L-3-methoxyphenlyalanine;FMOC-L-3-METHOXYPHENYLALANINE;FMOC-L-M-TYR(ME)
• CAS NO: 206060-40-4
• Molecular Formula: C25H23NO5
• Molecular Weight: 417.45
• Mol File: 206060-40-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0-5°C
• CAS DataBase Reference: FMOC-L-3-METHOXYPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-3-METHOXYPHENYLALANINE(206060-40-4)
• EPA Substance Registry System: FMOC-L-3-METHOXYPHENYLALANINE(206060-40-4)

Safety Data

• Hazardous Substances Data: 206060-40-4(Hazardous Substances Data)

Usage

General Description

FMOC-L-3-Methoxyphenylalanine is a chemical compound used often in the field of organic chemistry, particularly in peptide synthesis. It essentially serves as a protective agent for the amino acid known as phenylalanine, which plays a role in the production of various proteins within the human body. This chemical features the FMOC protecting group, which helps to prevent unwanted side reactions during the synthesis process. Additionally, its methoxyphenylalanine component contributes to its hydrophobic nature, which is a significant factor in the effectiveness of peptide-based therapeutics.

Relevant articles and documents

Ligand-enabled β-C-H arylation of α-amino acids using a simple and practical auxiliary

Pd-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asymmetric synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. We previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein we report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive molecules, and chiral bis(oxazoline) ligands.