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

Name: (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 220498-02-2
Cat. No. CS-W013879
Purity≥98%
MDL No.MFCD01311783

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(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid|CS-W013879

Structure of 220498-02-2

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General Information

CAS No. 220498-02-2
Cat. No. CS-W013879
Purity ≥98%
MDL No. MFCD01311783
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₁NO₄
Molecular Weight 387.43
Synonym(s) None
SMILES O=C(C[C@H](C1=CC=CC=C1)NC(OCC2C3=C(C=CC=C3)C4=C2C=CC=C4)=O)O

Description

(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid features a chiral, bench-stable backbone with a fluorenylmethoxycarbonyl (Fmoc) protecting group, enabling direct incorporation into peptide synthesis workflows. The pendant phenyl moiety imparts enhanced solubility and structural rigidity, facilitating efficient coupling reactions under standard conditions.

Application

(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid serves as a robust chiral building block for peptide synthesis, offering high stereochemical integrity and bench stability. The Fmoc group enables orthogonal protection, facilitating efficient deprotection under mild basic conditions. Its phenyl-substituted aliphatic side chain provides structural rigidity and enhances compatibility with standard coupling protocols, making it ideal for the synthesis of complex peptide architectures and bioactive scaffolds.

Synthesis

Route1
- In-stock
  
  614-19-7
- 28920-43-6
- ~75%
- In-stock
  
  220498-02-2
References
- Terracciano, Stefania; Bruno, Ines; D'Amico, Elisabetta; Bifulco, Giuseppe; Zampella, Angela; Sepe, Valentina; Smith, Charles D.; Riccio, Raffaele Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 13 p. 6580 - 6588
Route2
- In-stock
  
  102410-65-1
- ~%
- In-stock
  
  220498-02-2
References
- Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, , vol. 43, # 10 p. 2152 - 2158
Route3
- In-stock
  
  111524-95-9
- ~%
- In-stock
  
  220498-02-2
References
- Synthesis, , # 6 p. 837 - 841

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

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 4.7411
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Building Blocks Functional Group Fmoc

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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

CAS No. 220498-02-2

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