**Deoxy‐hydroxylamino‐sugar Derivatives and Corresponding Diglycosylnitroxides Radicals** A number of sugar aldonitrones, including __C,N__‐diglycosylnitrones, and ketonitrones have been treated with __Grignard__ reagents or cyanide anion leading to the corresponding deoxy‐hydroxylamino‐sugars. On
Dérivés C-glycosyliques XXIII. Radicaux libres stables dérivés de sucre Communication préliminaire
✍ Scribed by Jean M. J. Tronchet; Eva Mihaly; Michel Geoffroy
- Publisher
- John Wiley and Sons
- Year
- 1975
- Tongue
- German
- Weight
- 276 KB
- Volume
- 58
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Treated with 2,3‐dimethyl‐2,3‐bis‐(hydroxylamino)‐butane, aldehydo‐dialdofuranoses (1) gave a mixture of two compounds: a 1,3‐dihydroxyimidazolidine (2) and a 1‐hydroxyimidazoline (3). Oxidation (PbO~2~) of compounds 3 gave stable free radicals having the structure of 2‐C‐Glycosyl‐4,4,5,5‐tetramethylimidazolines 1‐oxyl (4), whereas 2‐C‐Glycosyl‐4,4,5,5‐tetramethylimidazolines 3‐oxide 1‐oxyl (5) were formed by oxidation of 2. The ESR. spectra of compounds 4 and 5 establish the structure of the imidazoline part of these radicals and provide informations on the sugar moiety.
📜 SIMILAR VOLUMES
**Some more examples of stable free radicals of carbohydrate heterocyclic derivatives** 2‐Glycosyl‐4,4,5,5‐tetramethylimidazoline‐ 3‐oxide‐1‐oxyls and 2‐glycosyl‐4,4,5,5‐tetramethylimidazoline 1‐oxyls have been prepared in nine carbohydrate series, which proves the generality of the method. The hyp
**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 f
## Abstract The syntheses of three types of sugar nitrones (aldonitrone, ketonitrone and α‐β unsaturated aldonitrone) are described. On 1,3‐dipolar cycloaddition with phenylacetylene, the aldonitrone gave two Δ~4~‐isoxazolines epimeric at the new asymetric carbon, while the same reaction on the ket
## Abstract __S__‐Methylation of 6‐__S__‐benzyl‐6‐deoxy‐1,2‐__O__‐isopropylidene‐3‐__O__‐methyl‐α‐D‐__xylo__‐6‐thiohexofuranos‐5‐ulose (**1**) gave the expected sulfonium salt **2** which on alcaline treatment yielded the stable sulfur ylide **3**. This compound constitutes an useful synthetic inte
## Abstract 1,2‐O‐Isopropylidene‐3‐O‐methyl‐α‐D‐__xylo__‐pentodialdo‐1,4‐furanose and its 3‐O‐benzyl analog have been reacted with pyridinyl‐3‐methylenetriphenylphosphorane and benzimidazolyl‐2‐methylenetriphenylphosphorane. The unsaturated sugars so obtained are vinylogs of homo‐C‐glycosides whose