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Ylides du soufre dérivés de sucres Communication préliminaire

✍ Scribed by Jean M. J. Tronchet; Hansjörg Eder

Publisher
John Wiley and Sons
Year
1975
Tongue
German
Weight
206 KB
Volume
58
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 intermediate in carbohydrate chemistry. On heating in 1,2‐dimethoxyethane, it underwent a Stevens rearrangement which led to an extension of the carbon chain of the sugar and, reacted with Michael acceptors, it gave cyclopropanation reactions.

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