65358-15-8Relevant academic research and scientific papers
2′-Deoxy-1-methylpseudocytidine, a stable analog of 2′-deoxy-5-methylisocytidine
Kim, Hyo-Joong,Leal, Nicole A.,Benner, Steven A.
, p. 3728 - 3732 (2009)
2′-Deoxy-5-methylisocytidine is widely used in assays to personalize the care of patients infected with HIV, hepatitis C, and other infectious agents. However, oligonucleotides that incorporate 2′-deoxy-5-methylisocytidine are expensive, because of its in
A practical synthesis of N1-methyl-2'-deoxy-ψ-uridine (ψ-thymidine) and its incorporation into G-rich triple helix forming oligonucleotides
Bhattacharya,Devivar,Revankar
, p. 1269 - 1287 (2007/10/02)
A convenient synthesis of N1-methyl-2'-deoxy-ψ-uridine (ψ-thymidine, ψT, 7a) has been accomplished in good yield. The structural conformation of 7a was derived by 2D NMR and 1D NOE experiments. The nucleoside 7a has been incorporated into G-rich triplex f
Nucleosides. 121. Improved and General Synthesis of 2'-Deoxy C-Nucleosides. Synthesis of 5-(2-Deoxy-β-D-erythro-pentofuranosyl)uracil, -1-methyluracil, -1,3-dimethyluracil, and -isocytosine
Pankiewicz, Krzysztof,Matsuda, Akira,Watanabe, Kyoichi A.
, p. 485 - 488 (2007/10/02)
5-(2-Deoxy-β-D-erythro-pentofuranosyl)-1,3-dimethyluracil (6a), -1-methyluracil (6b), -uracil (6c), and -isocytosine (6d) were synthesized.Compounds 6b-d are C-nucleoside isosteres of thymidine, 2'-deoxyuridine, and 2'-deoxycytidine, respectively. 1,3-Dimethylpseudouridine (1a), 1-methylpseudouridine (1b), pseudouridine (1c), and pseudoisocytidine (1d) were treated with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane in pyridine to afford the corresponding 3',5'-tetraisopropyldisiloxanyl derivatives 2 which were converted into the respective 2'-O- C-nucleosides 3.Compounds 3a,b were converted directly into the corresponding 2'-deoxy β-C-nuleosides 5a,b exclusively by reduction with n-Bu3SnH.For the synthesis of 2'-deoxy β-C-nucleosides 5c,d, the intermediates 3c,d were trimethylsilylated prior to n-Bu3SnH treatment.Deprotection of 5a-d was effected by treatment with n-Bu4NF, and the corresponding free 2'-deoxy β-C-nucleosides 6a-d were obtained in good yields.
