Ylides du soufre dérivés de sucres Communication préliminaire |
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Authors: | Jean M. J. Tronchet,Hansj rg Eder |
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Affiliation: | Jean M. J. Tronchet,Hansjörg Eder |
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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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