Functionalization of guanosine and 2'-deoxyguanosine at C6: a modified Appel process and S(N)Ar displacement of imidazole.
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.
Janeba
Zlatko
Z
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Lin
Xiaoyu
X
Robins
Morris J
MJ
D003849:Deoxyguanosine / Q000031:analogs & derivatives / Q000737:chemistry*; D006151:Guanosine / Q000031:analogs & derivatives / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*
D007093:Imidazoles; D006151:Guanosine; C029899:imidazole; D003849:Deoxyguanosine