O-Unprotected glycosyltriazenes are prepared for the first time by coupling of 1-anthraquinone-1-diazonium hydrogensulfate with β-glycopyranosylamines to afford 1- (anthraquinone-1-yl)-3-( β-glycopyranosyl)triazenes 3a—h. Acetylation of compounds 3 furnished the O-acetates 4a—g. The stability of triazenes 3 results from fixation of the NH proton in an intramolecular hydrogen bond to one of the anthraquinone carbonyl oxgen atoms. Treatment of triazenes 4 with tert-butyl hypochlorite afforded acetoglycosyl chlorides 6 and 1-azidoanthraquinone 7. With acetic acid the triazene 4a formed tetra-O-acetyl-D-xylopyranose 9 together with 1- aminoanthraquinone 10.

Preparation of Glycosyltriazenes

In this paper we describe a high-yielding method leading to a novel family of sugars: the sugar triazene N-oxides. The anticonvulsant effect of one of these compounds was tested. It showed a promising activity indicating the potential therapeutic usefulness of this class of carbohydrate derivatives.

Tronchet Jm

Papers

[Synthesis and anticonvulsant properties of sugar triazene N-oxides].

Syntheses and Anticonvulsant Properties of Sugar Triazene N‐Oxides.