title: Functionalization of guanosine and 2'-deoxyguanosine at C6: a modified Appel process and S(N)Ar displacement of imidazole.
abstract: Treatment of sugar-protected 2-N-trityl derivatives of guanosine and 2'-deoxyguanosine with imidazole/triphenylphosphine/iodine/ethyldiisopropylamine gives the corresponding 6-(imidazol-1-yl)-2-(tritylamino)purine nucleosides. S(N)Ar displacement of the imidazole moiety with nucleophiles provides 2-amino-6-substituted-purine nucleosides and 2'-deoxynucleosides.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
authors.forename: Zlatko
authors.initials: Z
authors.lastname: Janeba
authors.forename: Xiaoyu
authors.initials: X
authors.lastname: Lin
authors.forename: Morris J
authors.initials: MJ
authors.lastname: Robins
mesh_terms: D003849:Deoxyguanosine / Q000031:analogs & derivatives / Q000737:chemistry*; D006151:Guanosine / Q000031:analogs & derivatives / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*
chemical_list: D007093:Imidazoles; D006151:Guanosine; C029899:imidazole; D003849:Deoxyguanosine