Research Projects

C-aryl glycosides belongs to a class of natural and/or synthetic bioactive compounds of pharmaceutical interest because of their wide range of biological activities and medicinal importance. Both the synthetic and natural C-glycosides possessing appealing biological properties that may have potential application in many areas of medicinal chemistry. Natural C-glycosides found in such as anti-tumor antibiotics, glycosylated flavonoids and the compound includes C-mannosyl tryptophan in glycoproteins, a posttranslational modification found in proteins belonging to the TSR family, aryl C-nucleosides, and C-glycosyl porphyrin. In 2010, C-glycosides of phlorozin, were introduced in the US market as an antidiabetic drug for the treatment of type 2 diabetes. Owing to the huge importance of both natural and synthetic C-glycosides numerous synthetic procedures based on a range of methodologies have been described in recent times. The development of new stereoselective and more synthetically robust procedures is still desirable due to fact that many methodologies either suffer from poor selectivity at anomeric carbon or poor substrate scope. We hypothesized that glycals can be utilized for the construction of C-C linkage at the anomeric position. Due to the endocyclic ring oxygen, the C-1 position of glycals is highly electrophilic and can be easily converted into boronated glycals by the treatment with a strong base and borylating agent. It is well documented that boronates such as aromatic boronic acids have been extensively utilized in cross-coupling reactions. Taking advantage of these highly reactive coupling partners we thought that vinylic boronates of glycals could be an effective synthon for stereoselective C-C bond formation in carbohydrates. All the library of newly synthesised compounds could be tested against SARS-CoV-2. From a more fundamental point of view, the research project could provide an effective route towards the stereoselective synthesis of Cglycosides in general.