Three-component Passerini Reactions Of Glycosyl Isocyanides

Saccharide compounds are an important organic compound widely distributed in the natural world.They play an important role in the process of life activities and they are the main source of energy of all living bodies for life activities.With the development of drugs,some saccharide drugs have been found to have antibiotic pharmacological effects,such as Erythromycin,Vancomycin and Teicoplanin;some saccharide drugs have anticoagulant effects,such as Heparin,the other saccharide drugs are used to treat diabetes,such as Acarbose and Voglibose,some polysaccharide drugs have inhibitory effects on tumor cells,such as swine fever,ginkgo and wolfberry.Nucleoside drugs are an important class of drugs that are used clinically to treat viral infectious diseases,tumors and AIDS.Our previous research found that tetrahydroindol compounds have good anti-tumor activity.Given the unique chemical structure of saccharide compounds and their good effect in the ADME process,we prepared 2-（2-）methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)acetic by a condensation cyclization reaction,and glycosyl isocyanides by amino sugars,and the two with aldehydes or ketones for the Passerini three-component reaction.11three-component amide compounds were synthesized,including 9α-configuration products and 2β-configuration products.The specific synthesis route and product chemical structure are as follows:Synthetic route:1.Prepare 2-（2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl）acetic acid by a condensation cyclization reaction2.Passerini three-component reaction（for an example:α-configuration glycosyl isocyanides）Product structure:α-configuration product: β-configurationproduct:R=CH₃CH₂CH₂,H,Ph CH₂CH₂,Ph CH₂,R=（CH₃）₂CH₂CH₂,H（CH₃）₃C,CH₃CH₂CH₂CH₂,CH₃,CH₃CH₂,（CH₂）₅None of these compounds were reported in the literature,and the structures of the target compounds were identified by HRMS,One-dimensional and two-dimensional NMR（1D,2D NMR）.