69534-68-5Relevant academic research and scientific papers
Unsaturated Carbohydrates. Part 22. Alkenes from 5-Bromohexopyranose Derivatives
Blattner, Regine,Ferrier, Robert J.,Tyler, Peter C.
, p. 1535 - 1539 (2007/10/02)
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.
