《Synthesis of C-Nucleoside Analogues2-[2-(Hydroxymethyl)-1, 3- dioxolan-5-yl]1, 3-thiazole-4-carboxamide and 2-[2-(Mercaptometh- yl)-1, 3-dioxolan-5-yl]1, 3-thiazole-4-carboxamide》.pdfVIP

Chinese Chemical Letters Vol. 15, No. 2, pp 163 – 166, 2004 163 /journal/ccl.html Synthesis of C-Nucleoside Analogues: 2-[2-(Hydroxymethyl)-1, 3- dioxolan-5-yl]1, 3-thiazole-4-carboxamide and 2- [2-(Mercaptometh- yl)-1, 3-dioxolan-5-yl] 1, 3-thiazole-4-carboxamide Dong Mei CAI, Min Jie LI, Da Liang LI, Tian Pa YOU* Department of Chemistry, University of Science and Technology of China, Hefei 230026 Abstract: Novel C-nucleosides of tiazofurin analogue (2-[2-(hydroxymethyl)- 1, 3-dioxolan-5-yl]1, 3-thiazole-4-carboxamide) and its thiol-substituted derivative (2-[2-(mercaptomethyl)-1,3-dioxolan -5-yl]1, 3-thiazole-4-carboxamide) were synthesized from methyl acrylate through a multistep 1 13 procedure. Their structures were confirmed by IR, HNMR, CNMR and elemental analysis. Keywords: C-Nucleosides, tiazofurin, selenazofurin, 1, 3-dioxolane, thiol-substituted. C-Nucleosides are an unique class of nucleosides in which the glycosidic chain is connected to the pendant heterocyclic base by a C-C bond instead of the C-N bond of the natural nucleosides. As a result, they are resistant to the chemical and the enzymatic hydrolytic cleavage of the glycosidic bond. Among the synthetic C-nucleosides, tiazofurin(2--D-ribofuranosylthizole-4-carboxamide NSC-286193)1