Studies On The Synthesis And Stereo-Structure Of Glycosyl Functional Compounds

As informational molecules, carbohydrates play essential roles in living organisms, including determination of antigenecity of molecules and phenotype of cells, recognition in many physiological and pathological events, and as signals of dynamic regulations and of regulation on time and space. Carbohydrate derivatives have been extensively investigated, including synthesis, characterization and biological activity, partly due to the facts that many naturally occurring saccharides and synthesized analogues exhibit various and potent biological activities, and have been widely employed as agrochemicals and pharmaceuticals.In this dissertation, glycosyl has been inducted into the structures of thiourea, diacylhydrazine, ferrocene, triazole, thiadiazole and triazine, using glycosyl isothiocyanates as intermediates. 65 compounds of seven series of glycosides have been designed and synthesized, among them 52 compounds have not been reported in literature. Their chemical structures have been confirmed by means of elemental analysis, IR1 or HNMR. Some of them have been studied by X-ray diffraction technique, and their crystal structures are reported precisely. Some properties of glycosides are also discussed here. The contents and the primary contributions of the research are summarized as follows:(1) Several novel highly symmetric carbohydrate compounds bearing diacylhydrazine framework have been synthesized via a five-step procedure, utilizing D-glucose, D-glactose and D-xylose as starting materials, respectively. They have been expected to display various bioactivities.(2) Several novel N-[(1-ferrocenylethylidene)amino]-N'-β-D-glycopyranosyl-thiourea have been efficiently synthesized via a six-step procedure, utilizing three monosaccharides (D-glucose, D-galactose and D-xylose) as starting materials, respectively. They have been preliminarily determined to display biological activityagainst certain fungi.(3) A series of novel Schiff base compounds bearing glycosyl have been synthesized. The induction of life matter may efficiently improve their biological activities.(4) Thioureas are known to exhibit broad spectrum of biological activities, but their solubility in water or in lips is not satisfied. So they have been modified with glycosyl and synthesized a series of novel N-Ar/R-N '-glycosyl thiourea compounds to improve their solubility.(5) Investigation of the substitute modification of triazole[3,4-6]-1,3,4-thiadiazoles has long been the focus of drug synthesis. Inducting glycosyl to them is very important undoubtedly. Encouraged by all these observations, a series of novel glycosyl-triazole[3,4-6]-1,3,4-thiadiazoles have been synthesized.(6) The compounds bearing different groups, which have different biological activity, show high biological activities. Encouraged by all these observations, a series of novel compounds have been synthesized, which bear glycosyl, thiadizole and triazine.(7) Novel glycosyl thiocarbamates, which have the potential to possess bioactivity, have been successfully prepared by using glycosyl isothiocyanates as intermediates.(8) Nine novel single crystals of glycosyl functional compounds have been successfully prepared and studied by X-ray diffraction technique. Their crystal structures are reported precisely, including bond lengths, bond angles, torsion angles and so on. Their crystals are classified into four series: glycosyl isothiocyanates, N-glycosyl thiocarbamates, xylosyl thiourea and glycosyl Schiff bases.(9) The configuration of the glycosides and their transformation in reaction are reported in this dissertation. The electrochemical actives, biological activities and thermal stability of some glycosides are also discussed.