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Updated: Jul 8, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Synthesis and biological evaluation of guanidine-type iminosugars
Matilde Aguilar1, Paula Díaz-Pérez, M Isabel García-Moreno
1Departamento de Química OrgAnica, Facultad de Química, Universidad de Sevilla, Profesor García GonzAlez 1, E-41012 Sevilla, Spain.
Abstract:
The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose --> piperidine rearrangement of 5-deoxy-5-guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.
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