Synthesis of 4-<i>O</i>-Alkylated <i>N</i>-Acetylneuraminic Acid Derivatives.

Johansson, Emil; Caraballo, Rémi; Elofsson, Mikael

Synthesis of 4-O-Alkylated N-Acetylneuraminic Acid Derivatives.

Johansson, Emil; Caraballo, Rémi; Elofsson, Mikael.

Afiliación

Johansson E; Department of Chemistry, Umeå University, Umeå SE90187, Sweden.
Caraballo R; Department of Chemistry, Umeå University, Umeå SE90187, Sweden.
Elofsson M; Department of Chemistry, Umeå University, Umeå SE90187, Sweden.

J Org Chem ; 86(13): 9145-9154, 2021 07 02.

Article en En | MEDLINE | ID: mdl-34138565

RESUMEN

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.

Asunto(s)

Ácido N-Acetilneuramínico; Ácidos Siálicos

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácidos Siálicos / Ácido N-Acetilneuramínico Idioma: En Revista: J Org Chem Año: 2021 Tipo del documento: Article País de afiliación: Suecia Pais de publicación: Estados Unidos

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