Unsaturated carbohydrates. Part 20. Direct conversion of phenyl 1-thiohexoside esters into phenyl 1-thiohex-1-enopyranosid-3-ulose esters
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 18,p. 1993-1996
- https://doi.org/10.1039/p19770001993
Abstract
Treatment of phenyl 1-thiohexoside esters with an excess of N-bromosuccinimide in refluxing carbon tetrachloride and under bright visible light caused them to be converted directly into the corresponding phenyl 1-thiohex-1-enopyranosid-3-ulose esters. Whereas the reactions with benzoates proceeded smoothly and in high yield, acetates gave mixtures of products which contained minor proportions of 2-monobromoacetyl analogues of the main enones. Glycosides with equatorial phenylthio-groups reacted appreciably faster than did their anomers.Keywords
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