(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methyl-3-phenylpropanoic acid

Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methyl-3-phenylpropanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 135944-05-7
Cat. No. CS-0101123
Purity≥98%
MDL No.MFCD02682285

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methyl-3-phenylpropanoic acid|CS-0101123

Structure of 135944-05-7

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General Information

CAS No. 135944-05-7
Cat. No. CS-0101123
Purity ≥98%
MDL No. MFCD02682285
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₅H₂₃NO₄
Molecular Weight 401.45
Synonym(s) Fmoc-Alpha-Methyl-L-Phe
SMILES O=C(O)[C@@](CC1=CC=CC=C1)(C)NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O

Description

This chiral building block features a fluorenylmethoxycarbonyl-protected amino acid scaffold with a sterically hindered α-methyl group and a phenyl-substituted β-carbon. The (S)-configuration enables stereoselective peptide synthesis, while the fluoren-9-ylmethoxycarbonyl moiety provides orthogonal protection and enhanced solubility under standard coupling conditions.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methyl-3-phenylpropanoic acid serves as a robust chiral building block for peptide synthesis, enabling efficient incorporation of sterically hindered β-branched amino acid residues. Its Fmoc group ensures excellent stability and orthogonal deprotection under mild basic conditions, while the phenyl and methyl substituents provide defined stereochemical control and enhanced structural rigidity. The compound facilitates high-yielding coupling reactions and simplifies purification through crystallization or standard chromatography.

Synthesis

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  135944-05-7
References
- Ceruso, Marco A.; McComsey, David F.; Leo, Gregory C.; Andrade-Gordon, Patricia; Addo, Michael F.; Scarborough, Robert M.; Oksenberg, Donna; Maryanoff, Bruce E. Bioorganic and Medicinal Chemistry, 1999 , vol. 7, # 11 p. 2353 - 2371

Safety Information

Download SDS

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 75.63
LogP 4.6111
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fmoc

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)amino)-2-methyl-3-phenylpropanoic acid

CAS No. 135944-05-7

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