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Dérivés C-glycosyliques. VII. Synthèse et réactions de nitrones dérivées de sucres. Communication préliminaire

✍ Scribed by J. M. J. Tronchet; Melle E. Mihaly

Publisher
John Wiley and Sons
Year
1972
Tongue
German
Weight
368 KB
Volume
55
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 ketonitrone led to a spiro‐Δ~4~‐isoxazoline. The reaction of these nitrones with carbon nucleophiles like phenylethynylmagnesium bromide constitutes a novel chain‐extension reaction in carbohydrate chemistry.

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