From Pyranosuloses and Pyranosenuloses to Deoxy Hydroxyamino Sugars

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Abstract
Deoxy hydroxyamino sugars represent a potentially useful series of sugar analogs owing mainly to the fact that they oxidize spontaneously to nitroxide free radicals to give spin-labeled sugar derivatives whose structure is very close to that of the parent sugar.3 We describe herin two synthetic pathways towards these compounds, reduction of sugar oximes and conjugate addition to enolones derivatives, both in the pyranose series.