Synthesis of purin 2'-deoxynucleoside analogues by using thioglycosides: 2',3'-dideoxyguanosine

Abstract

Synthesis of purine 2'-deoxynucleoside analogues derivatives, named by using thioglycosides: 2',3'-dideoxyguanosine (3) and 2',3'-dideoxyguanosine (4) is described. This approach is based on condensation of S-glycoside (5) with silylated heterocyclic based (6,7) using N-bromosuccinimide as promoter. It is know that in the process of glycosylation reaction a mixture of three isomers, namely aN9, aN7 and bN7 is formed besides the desired bN9. In order to prevent undered formation of N7 isomers 2-aminogroup of adenine and 6-oxogroupvof guanine were modified by bulky protective gpoups