Effective anomerisation of 2'-deoxyadenosine derivatives during disaccharide nucleoside synthesis |
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| Authors: | Gulyaeva Irina V Neuvonen Kari Lönnberg Harri Rodionov Andrei A Shcheveleva Elena V Bobkov Georgii V Efimtseva Ekaterina V Mikhailov Sergey N |
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| Affiliation: | Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia. |
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| Abstract: | The formation of a disaccharide nucleoside (11) by O3'-glycosylation of 5'-O-protected 2'-deoxyadenosine or its N6-benzoylated derivative has been observed to be accompanied by anomerisation to the corresponding alpha-anomeric product (12). The latter reaction can be explained by instability of the N-glycosidic bond of purine 2'-deoxynucleosides in the presence of Lewis acids. An independent study on the anomerisation of partly blocked 2'-deoxyadenosine has been carried out. Additionally, transglycosylation has been utilized in the synthesis of 3'-O-beta-D-ribofuranosyl-2'deoxyadenosines and its alpha-anomer. |
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