Synthesis of 4-O-Alkylated N-Acetylneuraminic Acid Derivatives | Zendy

Emil Johansson | Zendy; Rémi Caraballo | Zendy; Mikael Elofsson | Zendy

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

Author(s) -

Emil Johansson,

Rémi Caraballo,

Mikael Elofsson

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c00235

Subject(s) - chemistry , alkyl , alkylation , halide , n acetylneuraminic acid , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , sialic acid , biochemistry , catalysis

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.

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