Unsaturated carbohydrates. Part 22. Alkenes from 5-bromohexopyranose derivatives
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1535-1539
- https://doi.org/10.1039/p19800001535
Abstract
Base-catalysed elimination of hydrogen bromide from 5-bromo-β-D-glucopyranose penta-acetate and penta-benzoate gives predominantly the endocyclic products, whereas treatment with zinc–acetic acid affords a means of obtaining the exocyclic 6-deoxy-5-enose esters. All eight alkenes obtainable from these two bromo-compounds are reported together with their 1H and 13C n.m.r. spectra. Unsaturated compounds derived from penta-O-benzoyl-5-bromo-α-D-glucopyranose and acetylated 5-bromouronates are also reported. The conformations of all the alkenes are discussed and, in one case, the influences of the anomeric and allylic effects can be compared.Keywords
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