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

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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

About the Authors

G. D. Gungarova
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


A. I. Davydova
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


Yu. G. Kirillova
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


V. I. Shvets
M.V. Lomonosov Moscow State University of Fine Chemical Technologies, 86, Vernadskogo pr., Moscow 119571
Russian Federation


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For citation:


Gungarova G.D., Davydova A.I., Kirillova Yu.G., Shvets V.I. Synthesis of purin 2'-deoxynucleoside analogues by using thioglycosides: 2',3'-dideoxyguanosine. Fine Chemical Technologies. 2006;1(1):19-22. (In Russ.)

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ISSN 2410-6593 (Print)
ISSN 2686-7575 (Online)