(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-phenylacetic acid

Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-phenylacetic acid
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CAS No. 574739-36-9
Cat. No. CS-0151370
Molecule weight387.43
Purity≥98%
MDL No.MFCD01861296

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-phenylacetic acid|CS-0151370

Structure of 574739-36-9

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General Information

CAS No. 574739-36-9
Cat. No. CS-0151370
Purity ≥98%
MDL No. MFCD01861296
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₁NO₄
Molecular Weight 387.43
Synonym(s) Fmoc-Nalpha-methyl-L-phenylglycine
SMILES CN([C@@H](C1=CC=CC=C1)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C42

Description

This chiral building block features a fluorenylmethoxycarbonyl-protected amine and a phenyl-substituted alpha-carbon, enabling direct incorporation into peptide synthesis. The (S)-configuration ensures stereoselective coupling, while the fluoren-9-ylmethyl group facilitates clean deprotection under mild conditions.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-phenylacetic acid serves as a valuable chiral building block in peptide synthesis, enabling efficient incorporation of (S)-α-methylphenylalanine derivatives. The Fmoc group provides orthogonal protection for the amine, allowing selective deprotection under mild conditions. The methylated α-amino center enhances metabolic stability and conformational rigidity, while the phenyl side chain supports diverse downstream functionalization. Bench-stable and compatible with standard coupling protocols, it facilitates reliable access to bioactive peptidomimetics and complex heterocyclic scaffolds.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 66.84
LogP 4.6932
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Glycine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-phenylacetic acid

CAS No. 574739-36-9

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