Nucleosides, nucleotides and nucleic acids p. 1849 - 1864 (2004)
Update date:2022-08-03
Topics:
Gulyaeva, Irma V.
Neuvonen, Kari
Loennberg, Harri
Rodionov, Andrei A.
Shcheveleva, Elena V.
Bobkov, Georgii V.
Efimtseva, Ekaterina V.
Mikhailov, Sergey N.
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 α-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-β-D-ribofuranosyl-2′-deoxyadenosines and its α-anomer.
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