No abstract

Synthesis of 3-Deoxy-3-(hydroxyamino)furanose AcetalsReduction of sugar ketoximes with NaBH,CN under acidic conditions constitutes a good synthetic pathway to deoxy(hydroxyamino)sugar derivatives. These compounds which are useful building blocks for the preparation of analogs of various classes of biologically important carbohydrates are reasonably stable.

Es werden Wege zur Synthese von Desoxyhydroxy‐aminozuckern, wie z.B. (II), (IV), (V) [über (V) lassen sich Glykopeptid‐ Bindungen eines neuen Typs knüpfen, wie sie das Nitron (VI) aufweist], (VIII), (IX), (XI), (XIII) und (XVI), aufgezeigt (keine eingehenderen Darstellungsvorschriften), die eine strukturelle Verwandtschaft zu bestimmten biochemisch wichtigen Molekülen haben.

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 (1H‐NMR., 13C‐NMR., ESR.) of some of these compounds are reported.