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Synthèse de sucres aminés ramifiés. IV Synthèse de quelques dérivés nouveaux par l'intermédiaire d'une hexose-spiro-aziridine

✍ Scribed by Jean-Marc Bourgeois

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
759 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Treatment of 3‐C‐cyano‐1,2:5,6‐di‐O‐isopropylidene‐3‐O‐(toluene‐p‐sulfonyl)‐α‐D‐allofurannose with AlLiH~4~ yields a sugar‐spiro‐aziridine and a branched chain sulfonamide. Reaction mechanisms are briefly discussed and the configurations of the products obtained are proved by chemical reactions. With hydrogenation, the spiro compound is opened to a branched chain amino sugar with the same tertiary carbon as in vancosamine.

Several derivatives of this new compound are described: the 6‐deoxy sugars in series L and D and the pentose resulting from its oxidation by periodic acid. The conformation around C(4)–C(5) bond is deduced for three compounds from NMR. data.

📜 SIMILAR VOLUMES

Synthèse de sucres ramifiés et de sucres
Synthèse de sucres ramifiés et de sucres aminés ramifiés. Communication préliminaire
✍ Jean-Marc Bourgeois 📂 Article 📅 1973 🏛 John Wiley and Sons 🌐 German ⚖ 259 KB

## Abstract When treated with cyanide ion, 1,2:5,6‐di‐O‐isopropylidene‐α‐~D~‐__ribo__‐hexofuranos‐3‐ulose yields one or the other of the two corresponding epimeric cyanhydrines, depending on the experimental conditions. One of these epimers, reacted with ammonium cyanide, yields the corresponding a