The Synthesis Of Glycosyl Amine Analogues

Ureas, thioureas and their derivatives have strong antibacterial, antitumor activities. They also play an important role in organic synthesis as intermediates. Isoureas, isothioureas and their derivatives are excellent nitric-oxide synthase inhibitors in life for the treatment of septic shock and related inflammatory disorders, besides acting as insecticide, herbcide. They are also appreciated by synthetic chemists. Phosphorotriamides have strong pesticidal and antiviral action, some of them have become commodities. With glycosyl isocyanates and glycosyl isothiocyanates as intermediates, we put glycosyl into ureas and isoureas to get acetylglycosylureylene phosphoric triamides and glycosyl isothiobiurets. Subsequently, glycosyl isothiobiurets are cyclized by oxidizing agents to glycosyl cyclic isothioureas. From these new compounds, we hope to widen their antibacterial activities and improve their pharmacological action, and also make efforts to explore new medicines and pesticides. All new compounds have not been reported. Their structures were confirmed by elemental analysis and IR, 'H NMR, MS spectral data. Some parts of them were confirmed by 31P NMR spectral data. The major work of the thesis:1. The preparation of acetylglycosylureylene phosphoric triamides by the reaction of phosphorodiamidohydrazides with glycosyl isocyanate which not be isolated;2. The preparation of glycosyl isothiobiurets in high yield by the reaction of glycosyl isothiocyanates with isoureas or isothioureas;3. The preparation of 3-alkylthio-5-glycopyranosylamino-l,2,4-thiadiazoles by the oxidizing cyclization of glycosyl isothiobiurets.