Efficient syntheses of [2-(15)N]guanosine and 2'-deoxy[2-(15)N]guanosine derivatives.
Nucleophilic substitution of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine, prepared from guanosine, with N-tert-butyldimethylsilyl[(15)N]-phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[(15)N]phthalimidopurine derivative. Treatment of this with sodium 2-cyanoethoxide yielded the [2-(15)N]guanosine derivative. The 2'-deoxy[2-(15)N]guanosine derivative was also efficiently synthesized through a similar procedure.
Kamaike
Kazuo
K
Laboratory of Pharmaceutical Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Kayama
Yoshihiro
Y
Isobe
Mitsuhisa
M
Kawashima
Etsuko
E
D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009587:Nitrogen Isotopes
D009587:Nitrogen Isotopes; D003849:Deoxyguanosine