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