(S)-Ethyl 2-acetamido-3-(4-hydroxy-3,5-diiodophenyl)propanoate

Name: (S)-Ethyl 2-acetamido-3-(4-hydroxy-3,5-diiodophenyl)propanoate
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CAS No. 21959-36-4
Cat. No. CS-0186190
Molecule weight503.07
Purity≥98%
MDL No.None

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(S)-Ethyl 2-acetamido-3-(4-hydroxy-3,5-diiodophenyl)propanoate|CS-0186190

Structure of 21959-36-4

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General Information

CAS No. 21959-36-4
Cat. No. CS-0186190
Purity ≥98%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₅I₂NO₄
Molecular Weight 503.07
Synonym(s) N-Acetyl-3,5-diiodo-l-tyrosine ethyl ester
SMILES CCOC([C@@H](NC(C)=O)CC1=CC(I)=C(O)C(I)=C1)=O

Description

(S)-Ethyl 2-acetamido-3-(4-hydroxy-3,5-diiodophenyl)propanoate features a chiral center at the alpha carbon, enabling stereoselective synthesis in medicinal chemistry. The para-hydroxyl and diiodo substitution pattern on the aromatic ring imparts high electron density and enhanced metabolic stability. This configuration supports efficient coupling reactions under standard conditions, facilitating access to complex peptide-like architectures.

Application

(S)-Ethyl 2-acetamido-3-(4-hydroxy-3,5-diiodophenyl)propanoate serves as a key chiral building block for the synthesis of bioactive heterocycles and peptide-like scaffolds. Its pendant phenolic hydroxyl group enables facile derivatization, while the diiodophenyl moiety supports palladium-catalyzed cross-coupling reactions. The molecule exhibits good bench stability and facilitates efficient purification, making it well-suited for iterative synthetic campaigns in medicinal chemistry and process development.

Synthesis

Route1
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  300-39-0
- ~%
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  21959-36-4
References
- Journal of the American Chemical Society, , vol. 54, p. 3718,3724
Route2
- 96679-34-4
- ~%
- In-stock
  
  21959-36-4
References
- Journal of the American Chemical Society, , vol. 54, p. 3718,3724
Route3
- 3604-84-0
- ~%
- In-stock
  
  21959-36-4
References
- Journal of the American Chemical Society, , vol. 54, p. 3718,3724

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H319
Precautionary Statements : P305+P351+P338

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 2.2117
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Tyrosine and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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(S)-Ethyl 2-acetamido-3-(4-hydroxy-3,5-diiodophenyl)propanoate

CAS No. 21959-36-4

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