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Investigating Triorthogonal Chemoselectivity. Effect of Azide Substitution on the Triazine Core
Anamika Sharma1,2, Rotimi Sheyi1, Ashish Kumar1
1Peptide Science Laboratory, School of Chemistry and Physics , University of KwaZulu-Natal , Durban 4001 , South Africa.
Organic Letters
|September 19, 2019
Summary
This study demonstrates triorthogonal chemoselectivity for the first time using s-triazine. Three distinct nucleophilic substitutions were achieved on the same molecule under mild, biologically compatible conditions.
Area of Science:
- Organic Chemistry
- Chemical Biology
Background:
- Chemoselectivity is crucial for complex molecule synthesis.
- Developing orthogonal reaction sets enables sequential, selective functionalization.
Purpose of the Study:
- To report the first example of triorthogonal chemoselectivity.
- To demonstrate the sequential substitution of a tridentate scaffold with different nucleophiles.
Main Methods:
- Utilized s-triazine as a model system for tridentate substitution.
- Performed a series of 43 distinct nucleophilic substitution reactions.
- Conducted reactions under conditions compatible with biological systems.
Main Results:
- Successfully achieved three sequential substitutions on the s-triazine core.
- Demonstrated high chemoselectivity, allowing the use of different nucleophiles in each step.
- Confirmed reaction compatibility with biological conditions.
Conclusions:
- Established a novel triorthogonal chemoselective reaction system.
- The s-triazine model provides a versatile platform for complex chemical synthesis.
- This methodology holds potential for applications in chemical biology and drug discovery.
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