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Facile and efficient approach for the synthesis of N(2)-dimethylaminomethylene-2'-O-methylguanosine. 2010

Tsuyoshi Mukobata, and Yosuke Ochi, and Yuji Ito, and Shun-Ichi Wada, and Hidehito Urata
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.

A convenient method for the synthesis of N(2)-dimethylaminomethylene-2'-O-methylguanosine (1), which is a useful intermediate for oligonucleotide construction, was developed. We chose the di-tert-butylsilyl group and the triisopropylbenzenesulfonyl group as sugar and base protecting groups, respectively. These protecting groups were stable during the 2'-O-methylation step with MeI and NaH. Our six-step synthesis of 1 is easy to perform using commercially available reagents, and requires only three chromatographic purifications. Compound 1 was obtained in 56% yield from guanosine.

UI MeSH Term Description Entries
D008745 Methylation Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed) Methylations
D006151 Guanosine A purine nucleoside that has guanine linked by its N9 nitrogen to the C1 carbon of ribose. It is a component of ribonucleic acid and its nucleotides play important roles in metabolism. (From Dorland, 28th ed)
D006847 Hydrocarbons, Iodinated Hydrocarbon compounds with one or more HYDROGEN atoms substituted with IODINE. Iodinated Hydrocarbons
D017670 Sodium Compounds Inorganic compounds that contain sodium as an integral part of the molecule. Compounds, Sodium

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