The proposed project is devoted to the synthesis of 2-deoxy-C-glycosides, C-disaccharides, and related compounds. C-Glycosides, including 2-deoxy derivatives are widespread in nature. Many of them possess a wide spectra of biological activities, i.e., antibacterial, antiviral, antitumor. C-Glycosides and related compounds can also serve as non-hydrolyzable enzyme inhibitors and chiral precursors for synthesis of other biologically important compounds. In this project, a new, general, and highly stereoselective method for preparation of 2-deoxy-C-glycosides, C-disaccharides and related compounds is proposed. The approach is based on the reaction of ArSCl adducts of glycals with different carbon nucleophiles in the presence of Lewis acid or salt of Ag(I). 2-Deoxy-beta-C-glycosides will be synthesized by the reaction of ArSCl adducts of glycals with vinyl ethers, titanium enolates, and some other organometallic derivatives. Reaction of ArSCl adducts of glycals with activated aromatic compounds and aromatic organometallic nucleophiles will result in the preparation of aryl C-beta-glycosides. Synthesis of C-disaccharides and related compounds will be achieved by the ArSCl mediated coupling of glycals and/or exo-glycals. Desulfurization of the synthesized compounds will be accomplished using Raney nickel or Bu3SnH.
| Koikov, Leonid N; Smoliakova, Irina P; Liu, Hui (2002) One-pot synthesis of C-glycosylic compounds (C-glycosides) from D-glucal, p-tolylsulfenyl chloride and aromatic/heteroaromatic compounds in the presence of Lewis acids. Carbohydr Res 337:1275-83 |
| Han, M; Smoliakova, I P; Koikov, L N (2000) Stereoselective synthesis of C-[2-S-(p-tolyl)-2-thio-beta-D-galactopyranosyl] compounds using the reaction of TolSCl adducts of D-galactal with C-nucleophiles. Carbohydr Res 323:202-7 |
