Synthesis of 4-O-Alkylated N-Acetylneuraminic Acid Derivatives
| Autor: | Emil Johansson, Rémi Caraballo, Mikael Elofsson |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Primary (chemistry) 010405 organic chemistry Drug discovery Organic Chemistry Alkylation 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry lipids (amino acids peptides and proteins) N-Acetylneuraminic acid Alkyl |
| Zdroj: | The Journal of Organic Chemistry. 86:9145-9154 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The synthesis of 4-O-alkyl analogues of N-acetylneuraminic acid (Neu5Ac) and the scope of the reaction are described. Activated alkyl halides and sulfonates and primary alkyl iodides give products in useful yields. The utility of the methodology is exemplified using a thiophenyl Neu5Ac building block to synthesize a 4-O-alkyl DANA analogue. These results expand the toolbox of Neu5Ac chemistry with value in drug discovery and for the design of novel tools to study the biology of Neu5Ac lectins. |
| Databáze: | OpenAIRE |
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