(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid

Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 134486-00-3
Cat. No. CS-0100996
Molecule weight529.32
Purity≥98%
MDL No.MFCD00235906

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid|CS-0100996

Structure of 134486-00-3

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General Information

CAS No. 134486-00-3
Cat. No. CS-0100996
Purity ≥98%
MDL No. MFCD00235906
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₀INO₅
Molecular Weight 529.32
Synonym(s) Fmoc-L-3-Iodotyrosine
SMILES OC(C=C1)=C(I)C=C1C[C@@H](C(O)=O)NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O

Description

This fluoren-9-ylmethoxycarbonyl-protected chiral amino acid derivative features a para-hydroxy-iodophenyl side chain, enabling direct incorporation into peptide syntheses via solid-phase methods. The Cbz-like protecting group ensures stability under standard coupling conditions and facilitates selective deprotection during purification workflows.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid serves as a valuable chiral building block for peptide synthesis, enabling efficient incorporation of iodinated phenolic side chains. The Fmoc group provides excellent stability and orthogonal deprotection, while the 4-hydroxy-3-iodophenyl moiety offers a versatile handle for late-stage functionalization via cross-coupling. Bench-stable and readily purified by chromatography, it facilitates robust access to complex bioactive scaffolds in medicinal chemistry and API development.

Synthesis

Route1
- 70-78-0
- In-stock
  
  82911-69-1
- ~82%
- In-stock
  
  134486-00-3
References
- THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; GOODMAN, Zelda Patent: WO2005/18682 A2, 2005 ; Location in patent: Page/Page column 24-25 ; WO 2005/018682 A2
Route2
- In-stock
  
  112883-29-1
- ~93%
- In-stock
  
  134486-00-3
References
- Espuna, Gemma; Arsequell, Gemma; Valencia, Gregorio; Barluenga, Jose; Perez, Marta; Gonzalez, Jose M. Chemical Communications, 2000 , # 14 p. 1307 - 1308

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 95.86
LogP 4.5312
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 6

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Tyrosine and derivatives

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)-3-(4-hydroxy-3-iodophenyl)propanoic acid

CAS No. 134486-00-3

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