Facile and efficient approach for the synthesis of N(2)-dimethylaminomethylene-2'-O-methylguanosine.
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.
Mukobata
Tsuyoshi
T
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
Ochi
Yosuke
Y
Ito
Yuji
Y
Wada
Shun-Ichi
S
Urata
Hidehito
H
D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D008745:Methylation; D017670:Sodium Compounds / Q000737:chemistry
D006847:Hydrocarbons, Iodinated; D017670:Sodium Compounds; D006151:Guanosine; C524957:sodium hydride; C014055:methyl iodide; C024900:2'-O-methylguanosine