Radicaux libres dérivés de sucres. V. Dérivés d'osamines N‐hydroxylées et composés voisins Communication préliminaire

Abstract

Free sugar radicals. V. Deoxyhydroxylaminosugar derivatives and related compounds We describe several synthetic routes to deoxyhydroxylaminosugar derivatives of the type Glyc‐N(OH)‐R where Glyc stands for a sugar moiety linked by any of its C‐atoms except the anomeric one and R for one of the following substituants: H‐atom, acyl, phosphoryl groups, aminoacid or sugar residues. Compounds of the above structure are potentially close analogs, homoisosteres, NOH replacing O, of biochemically important molecules. Under aerobic conditions, solutions of these derivatives contain minute concentrations of the corresponding nitroxide radicals which do not decrease significantly the resolution of the NMR. spectra but render these compounds usable as a new kind of spin labels. Spectroscopic properties ( 1 H‐NMR., 13 C‐NMR., ESR.) of some of these compounds are reported.