The stereochemistry of a 2-S-ethyl-2-thioaldohexose: ready epimerization of a 2-thioaldose
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society D: Chemical Communications
- No. 17,p. 1038-1039
- https://doi.org/10.1039/c29700001038
Abstract
The acid-catalysed replacement of the C-2 hydroxy-group in 3,4,5,6-tetra-O-benzoyl-D-glucose diethyl dithioacetal (1) by an ethylthio-group proceeds with inversion of configuration, probably through an episulphonium-ion intermediate, to give the diethyl dithioacetal (2) of 2-S-ethyl-2-thio-D-mannose (9), the free sugar (9) being exceptionally readily epimerized, at pH 8, to give the gluco-analogue (8).Keywords
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