(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(4-(tert-butoxy)phenyl)butanoic acid

Name: (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(4-(tert-butoxy)phenyl)butanoic acid
Brand: ChemScene
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CAS No. 219967-69-8
Cat. No. CS-0132402
Purity≥95%
MDL No.MFCD01862862

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(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(4-(tert-butoxy)phenyl)butanoic acid|CS-0132402

Structure of 219967-69-8

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General Information

CAS No. 219967-69-8
Cat. No. CS-0132402
Purity ≥95%
MDL No. MFCD01862862
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₉H₃₁NO₅
Molecular Weight 473.56
Synonym(s) Fmoc-o-t-butyl-l-beta-homotyrosine
SMILES OC(C[C@H](CC1=CC=C(OC(C)(C)C)C=C1)NC(OCC2C3=CC=CC=C3C4=CC=CC=C24)=O)=O

Description

This fluorenylmethoxycarbonyl-protected amino acid derivative features a chiral center at the 3-position and incorporates a para-tert-butoxyphenyl group that enhances solubility and stability. The C-terminal carboxylic acid enables direct coupling in peptide synthesis, while the Fmoc moiety provides orthogonal protection. Designed for efficient solid-phase peptide assembly, this building block offers high reactivity under standard conditions and excellent handling characteristics.

Application

(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(4-(tert-butoxy)phenyl)butanoic acid serves as a robust chiral building block for peptide synthesis, leveraging the orthogonal stability of the Fmoc group and the bench-stable tert-butoxy aryl moiety. It facilitates efficient coupling reactions under standard conditions, enabling reliable access to complex peptidomimetics and bioactive scaffolds with high diastereoselectivity and minimal epimerization.

Synthesis

Route1
- 219967-66-5
- ~72%
- In-stock
  
  219967-69-8
References
- Abele, Stefan; Guichard, Gilles; Seebach, Dieter Helvetica Chimica Acta, 1998 , vol. 81, # 12 p. 2141 - 2156
Route2
- In-stock
  
  71989-38-3
- ~%
- In-stock
  
  219967-69-8
References
- Helvetica Chimica Acta, , vol. 81, # 12 p. 2141 - 2156

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 84.86
LogP 5.7884
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 8

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(4-(tert-butoxy)phenyl)butanoic acid

CAS No. 219967-69-8

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