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Nucleic acid component analogues: synthesis of 2'-deoxynucleosides from 5-substituted-4-hydroxy-6(1H)-pyrimidinones
Ahmed F Khattab1, Ahmed E S Abdel Megied, Erik B Pedersen
1Chemistry Department, Faculty of Science, Monoufiya University, Shebien El-Koam, A. R. Egypt. khattab2000@yahoo.com
Nucleosides, Nucleotides & Nucleic Acids
|April 24, 2003
Abstract:
Condensation of the silylated pyrimidines 5a-c with methyl 2-deoxy-3,5-di-O-toluoyl-D-pentofuranoside 6, using trimethylsilyltriflate as catalyst gave anomeric mixtures of 2'-deoxynucleosides 7a-c, the pure alpha- and beta-anomers were separated and deprotected with sodium methoxide in methanol to give 1-(2'-deoxy-alpha-D-pentafuranosyl)-4-hydroxy-5-substituted-6(1H)-pyrimidinones 10a,b and 13a and their corresponding beta-anomers 11a,b and 13b.