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Issue 21, 2012
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Intramolecular cyclization of alkoxyaminosugars: access to novel glycosidase inhibitor families

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Abstract

We report the synthesis of two novel families of iminosugars as glycosidase inhibitors involving an intramolecular cyclization between an N-alkoxyamino group and a latent aldehyde of a reducing sugar as the key step. Using this methodology we have prepared the hitherto unknown bicyclic polyhydroxylated N-(methoxy, benzyloxy)anhydroazepanes and N-benzyloxy-D-xylonojirimycin; all these novel compounds turned out to be moderate β-glucosidase inhibitors in a pH-dependent manner.

Graphical abstract: Intramolecular cyclization of alkoxyaminosugars: access to novel glycosidase inhibitor families

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Publication details

The article was received on 27 Jan 2012, accepted on 29 Mar 2012 and first published on 03 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB25213A
Citation: Org. Biomol. Chem., 2012,10, 4220-4228
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    Intramolecular cyclization of alkoxyaminosugars: access to novel glycosidase inhibitor families

    E. Martínez-Castro, A. González-Benjumea, Ó. López, I. Maya, E. Álvarez and J. G. Fernández-Bolaños, Org. Biomol. Chem., 2012, 10, 4220
    DOI: 10.1039/C2OB25213A

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