Facile synthesis of 1',2'-cis-beta-pyranosyladenine nucleosides.
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.
Ando
Takayuki
T
Center for Emerging Infectious Diseases, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.
Shinohara
Hisashi
H
Luo
Xiong
X
Kandeel
Mahmoud
M
Kitade
Yukio
Y
D000085:Acetates / Q000737:chemistry; D000225:Adenine / Q000737:chemistry*; D000241:Adenosine / Q000138:chemical synthesis*; D002164:Camphor / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D002586:Cesium / Q000737:chemistry; D002621:Chemistry / Q000379:methods; D005697:Galactosides / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry
D000085:Acetates; D002241:Carbohydrates; D005697:Galactosides; D005960:Glucosides; D009705:Nucleosides; D011687:Purines; D011714:Pyrans; D000644:Quaternary Ammonium Compounds; D013451:Sulfonic Acids; C007816:beta-galactoside; D002586:Cesium; D002164:Camphor; C009405:tetrabutylammonium; D000225:Adenine; D000241:Adenosine; C079308:6-chloropurine