N-Fmoc-4-(tert-butoxycarbonylmethoxy)-L-phenylalanine

Name: N-Fmoc-4-(tert-butoxycarbonylmethoxy)-L-phenylalanine
Brand: ChemScene
Availability: InStock
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CAS No. 181951-92-8
Cat. No. CS-0130196
Molecule weight517.57
Purity≥97%
MDL No.MFCD07781259

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N-Fmoc-4-(tert-butoxycarbonylmethoxy)-L-phenylalanine|CS-0130196

Structure of 181951-92-8

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General Information

CAS No. 181951-92-8
Cat. No. CS-0130196
Purity ≥97%
MDL No. MFCD07781259
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₀H₃₁NO₇
Molecular Weight 517.57
Synonym(s) None
SMILES O=C(O)[C@H](CC1=CC=C(OCC(OC(C)(C)C)=O)C=C1)NC(OCC2C3=CC=CC=C3C4=CC=CC=C24)=O

Description

N-Fmoc-4-(tert-butoxycarbonylmethoxy)-L-phenylalanine is a bifunctional amino acid derivative featuring a protected amine and a labile tert-butyl ester. This combination enables sequential conjugation in solid-phase peptide synthesis, where the Fmoc group facilitates deprotection under mild basic conditions, and the tert-butoxycarbonylmethoxy side chain offers a site for orthogonal functionalization or linker attachment.

Application

N-Fmoc-4-(tert-butoxycarbonylmethoxy)-L-phenylalanine serves as a versatile building block for peptide synthesis, enabling the introduction of a protected hydroxyphenyl side chain. The Fmoc group ensures orthogonal protection for amine functionality, while the tert-butoxycarbonyl moiety provides stable protection for the pendant alcohol. This derivative facilitates efficient coupling reactions and supports downstream deprotection strategies compatible with standard solid-phase and solution-phase workflows.

Synthesis

Route1
- In-stock
  
  82911-69-1
- 145544-50-9
- ~87%
- In-stock
  
  181951-92-8
References
- Burke Jr., Terrence R.; Yao, Zhu-Jun; Zhao, He; Milne, George W. A.; Wu, Li; Zhang, Zhong-Yin; Voigt, Johannes H. Tetrahedron, 1998 , vol. 54, # 34 p. 9981 - 9994
Route2
- 5292-43-3
- ~%
- In-stock
  
  181951-92-8
References
- Tetrahedron, , vol. 54, # 34 p. 9981 - 9994
Route3
- In-stock
  
  5513-40-6
- ~%
- In-stock
  
  181951-92-8
References
- Tetrahedron, , vol. 54, # 34 p. 9981 - 9994

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 111.16
LogP 4.9415
H_Acceptors 6
H_Donors 2
Rotatable_Bonds 9

Other Classifications

Bioactive Molecules Peptides

Building Blocks Functional Group Fmoc

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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N-Fmoc-4-(tert-butoxycarbonylmethoxy)-L-phenylalanine

CAS No. 181951-92-8

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