title: Effective anomerisation of 2'-deoxyadenosine derivatives during disaccharide nucleoside synthesis.
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.
authors.affiliation: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia.
authors.forename: Irina V
authors.initials: IV
authors.lastname: Gulyaeva
authors.forename: Kari
authors.initials: K
authors.lastname: Neuvonen
authors.forename: Harri
authors.initials: H
authors.lastname: Lönnberg
authors.forename: Andrei A
authors.initials: AA
authors.lastname: Rodionov
authors.forename: Elena V
authors.initials: EV
authors.lastname: Shcheveleva
authors.forename: Georgii V
authors.initials: GV
authors.lastname: Bobkov
authors.forename: Ekaterina V
authors.initials: EV
authors.lastname: Efimtseva
authors.forename: Sergey N
authors.initials: SN
authors.lastname: Mikhailov
mesh_terms: D003839:Deoxyadenosines / Q000138:chemical synthesis*; D004187:Disaccharides / Q000138:chemical synthesis*; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis*
chemical_list: D003839:Deoxyadenosines; D004187:Disaccharides; D009705:Nucleosides; C058118:2'-deoxyadenosine