Synthesis And Application Of Acetonyl-?-C-Glucoside Derivatives

C-Glycosides have received increasing attention in recent years because of their preferable properties in biological functions and stability against acidic or enzymatic hydrolysis.They are often used as a kind of vital building block in the synthesis of natural products and medicines.In this thesis,we have reported the synthesis of new C-glycosides with potential applications in the field of surfactant,natural product and fluorescent probe.1.?-C-furanoside and ?-C-pyranoside were synthesized respectively by acid and base catalyzation.Lewis acids catalyzing in the condensation of D-glucose and dibenzoylmethane to obtain(1R,2S,3S)-1-(5-phenylfuran-2-yl)butane-1,2,3,4-tetraol 2.2 has been reported.Experiments were carried out to determine the optimum conditions by varying the catalysts,solvents and temperatures.The structure of target compound was confirmed by NMR and HRMS.2.Selective mono-protection of diols in acetonyl-C-glucoside was studied.The esterification substrate 3.2 was synthesized over two steps in the total yield of 58%.Regioselective esterification resulted majorly into 3-substituted products.Results indicated that strong electron-withdrawing and large space steric hindrance of esterification reagents lead to regioselective substituted products.The X-ray diffraction analysis of 3-substitued product 3.4j was also researched.The factors leading to the stabilization of the crystal,including the edge-to-face ?-? interaction and hydrogen bonds were discussed.3.The synthesis and application of UV-visible C-glycolipid surfactant were studied.The C-glycolipids were synthesized over three steps.Compared with traditional alkyl glycoside surfactants,these kind of surfactants are UV-visible and can be tested by HPLC ultraviolet detector.Besides,all these newly synthesized compounds can be separated by recrystallization,which is economical and cost effective.4.Synthesis of C-furanosyl chalcone analogues of aspalathin have been carried out based on the similarity and association principle of drug design.The antioxidant activities and the anticancer activities were studied.Compound 5.2c appeared to be the most promising compound with good antioxidant ability(inhibition%= 63.55%)and inhibition towards Hep-G2 and MCF-7 cells,IC50 at 4.9?M,19?M respectively.The antioxidant abilities of C-furanosides and C-pyranosides were compared and noted that the C-pyranosides are more active.5.Synthesis and application of a novel water soluble fluorescent probe based on C-glycoside were researched.The comparison between carbohydrate-derived probe and none-carbohydrate-derived probe indicated that neutral probe with carbohydrate moiety showed more excellent hydrophily,biocompatibility and higher fluorescent intensity in water solution.DFT methods was used to study these eight compounds,which suggested that high electron density and large conjugated degree of probes were benefit for the fluorescent properties.Fluorescent spectroscopic studies showed that the as-prepared dye could be used in the labeling of BSA as the fluorescence of this dye was quenched in water and turned on after incubated with protein.The fluorescent intensity and the concentration of protein are of an excellent linear relation which indicated that the probe 6.1h could be used in the development of protein assay kit.Besides,compound 6.1h was preliminarily studied in the field of monitoring trypsin hydrolysis and cell staining.