Ando Takayuki, Shinohara Hisashi, Luo Xiong, Kandeel Mahmoud, Kitade Yukio
Center for Emerging Infectious Diseases, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.
Carbohydr Res. 2007 Dec 10;342(17):2641-8. doi: 10.1016/j.carres.2007.08.009. Epub 2007 Aug 23.
1',2'-cis-beta-Glycosyladenine nucleosides, such as beta-altroside, beta-mannoside, and beta-idoside, were efficiently synthesized from the corresponding 1',2'-trans-beta-6-chloropurine derivatives, beta-glucoside, and beta-galactoside. Nucleophilic substitution of the O-trifluoromethanesulfonyl groups at the C-2' and/or 3' was carried out using tetrabutylammonium acetate or cesium acetate under mild conditions. Subsequent deprotection and amidation afforded the desired compounds, 1',2'-cis-beta-pyranosyladenine nucleosides.
