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| - Chemoselective Glycosylation Strategy for the ConvergentAssembly of Phytoalexin-Elicitor Active Oligosaccharides andTheir Photoreactive Derivatives
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| - A highly convergent route for the synthesis of branched glucosides having phytoalexin-elicitoractivity has been developed. The readily available building blocks 2, 3, and 6 were used for theassembly of a core trisaccharide in two chemo- and regioselective glycosylations. Compound 7 wasconverted into the artificial spacer-containing glycosyl acceptor 9. Regioselective condensation offragment 7 with 9 led to the formation of fully protected hexasaccharide 14. Deprotection ofhexasaccharide 14 followed by the reaction with 4-azidosalicylate gave compound 1b. It wasestablished that compound 1b is a photoreactive compound. Reaction time and conditions wereestablished for photolysis of compound 1b and labeling with radioactive iodine. A soybean rootbinding site for an elicitor-active hepta-β-glucoside bound compound 1b with the same affinity asthe underivatized hepta-β-glucoside.
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