Allylic isomerisations of unsaturated carbohydrate derivatives. A new approach to the synthesis of amino, thio, and branched-chain sugars
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society D: Chemical Communications
- No. 21,p. 1385-1387
- https://doi.org/10.1039/c29700001385
Abstract
2,3-Unsaturated hexopyranoside derivatives with azido-, thiocyanato-, vinyloxy-, and (methylthio)-thiocarbonyloxy-groups at C-4 rearrange thermally to give 3,4-unsaturated isomers with azido-, isothiocyanato-, acetaldehydo-, and (methylthio)carbonylthio-groups attached to C-2; the asymmetry of C-4 in the initial compounds is transmitted to C-2 during the isomerisations.Keywords
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