Nucleic acid component analogues: synthesis of 2'-deoxynucleosides from 5-substituted-4-hydroxy-6(1H)-pyrimidinones.
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.
Khattab
Ahmed F
AF
Chemistry Department, Faculty of Science, Monoufiya University, Shebien El-Koam, A. R. Egypt. khattab2000@yahoo.com
Abdel Megied
Ahmed E S
AE
Pedersen
Erik B
EB
D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009696:Nucleic Acids / Q000737:chemistry; D011744:Pyrimidinones / Q000737:chemistry*
D003853:Deoxyribonucleosides; D009696:Nucleic Acids; D011744:Pyrimidinones