Carbohydrate Research 2007-12-10

Facile synthesis of 1',2'-cis-beta-pyranosyladenine nucleosides.

Takayuki Ando, Hisashi Shinohara, Xiong Luo, Mahmoud Kandeel, Yukio Kitade

Index: Carbohydr. Res. 342(17) , 2641-8, (2007)

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Abstract

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.