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Ylides du soufre dérivés de sucres Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Eder Hansjörg
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580632
Subject(s) - chemistry , sulfonium , ylide , sulfur , dimethoxyethane , medicinal chemistry , cyclopropanation , stereochemistry , organic chemistry , salt (chemistry) , catalysis , electrode , electrolyte
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.