Effective Anomerisation of 2′-Deoxyadenosine Derivatives During Disaccharide Nucleoside Synthesis

• Published in: Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2004-01, Vol.23 (12), p.1849-1864
• Main Authors: Gulyaeva, Irina V., Neuvonen, Kari, Lönnberg, Harri, Rodionov, Andrei A., Shcheveleva, Elena V., Bobkov, Georgii V., Efimtseva, Ekaterina V., Mikhailov, Sergey N.
• Format: Article
• Language: English
• Subjects: 2′-Deoxyadenosine derivatives; Anomerisation; Deoxyadenosines - chemical synthesis; Disaccharide nucleosides; Disaccharides - chemical synthesis; Nucleic Acid Conformation; Nucleosides - chemical synthesis; Synthesis
• ISSN: 1525-7770; 1532-2335
• DOI: 10.1081/NCN-200040627

The formation of a disaccharide nucleoside (11) by O3′-glycosylation of 5′-O-protected 2′-deoxyadenosine or its N 6 -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.