Toward fluorinated aminoglycosides: Structural studies of phenylhydrazine condensation with carbohydrate derivatives

Description

The reaction of phenylhydrazine with a sugar dialdehyde in water, as a key step for the synthesis of the 3-amino-3-deoxy-d-glucose moiety contained in kanamycin, has been revisited. Structural studies (IR and NMR as well as a simple theoretical model based on energy-minimization calculations and MD calculations) reported herein support the observed stereo- and regioselectivity. Efforts to improve the reproducibility and viability of the process as part of a convenient approach towards fluorinated kanamycin are also now presented.

Abstract

Agencia Española de Cooperación Internacional para el Desarrollo A/023577/09 A/030422/10

Abstract

Junta de Andalucía FQM 142 P09-AGR-4597

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