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

Name: 3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 180181-93-5
Cat. No. CS-0149774
Purity≥97%
MDL No.MFCD01863192

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Type	HazMat Fee
Excepted Quantity	$0.00
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3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid|CS-0149774

Structure of 180181-93-5

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General Information

CAS No. 180181-93-5
Cat. No. CS-0149774
Purity ≥97%
MDL No. MFCD01863192
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₁NO₄
Molecular Weight 387.43
Synonym(s) 3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-phenylpropanoic acid
SMILES O=C(O)CC(NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)C4=CC=CC=C4

Description

This fluorenylmethoxycarbonyl-protected amino acid derivative features a sterically hindered, electron-rich fluoren-9-ylmethoxy carbonyl group that enables efficient coupling in peptide synthesis. The pendant phenylpropanoic acid moiety enhances solubility and stability under standard conditions, facilitating robust N-terminal protection and subsequent deprotection without racemization.

Application

3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid serves as a robust amino acid derivative for peptide synthesis, offering enhanced solubility and stability during coupling steps. The Fmoc group enables efficient deprotection under mild basic conditions, while the phenyl-substituted propanoic acid backbone provides a rigid, hydrophobic side chain useful in peptidomimetic design. Its compatibility with standard solid-phase protocols and ease of purification make it a practical choice for synthesizing biologically active peptides and scaffold libraries.

Synthesis

Route1
- 28920-43-6
- 3646-50-2
- ~99%
- In-stock
  
  180181-93-5
References
- Sulyok; Gibson; Goodman; Hoelzemann; Wiesner; Kessler Journal of Medicinal Chemistry, 2001 , vol. 44, # 12 p. 1938 - 1950
Route2
- 3646-50-2
- In-stock
  
  82911-69-1
- ~%
- In-stock
  
  180181-93-5
References
- EP1135374 B1, ; Page/Page column 22 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS08,GHS09
Signal Word : Danger	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H315-H319-H335-H372-H410
Precautionary Statements : P233-P260-P261-P264-P270-P271-P273-P280-P302+P352-P304+P340-P330-P340-P362-P391-P403-P405-P501

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Computational Chemistry Data

TPSA 75.63
LogP 4.7411
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 180181-93-5

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