Effective anomerisation of 2 '-deoxyadenosine derivatives during disaccharide nucleoside synthesis

: Gulyaeva IV, Neuvonen K, Lonnberg H, Rodionov AA, Shcheveleva EV, Bobkov GV, Efimtseva EV, Mikhailov SN

Publisher: TAYLOR & FRANCIS INC

: 2004

Nucleosides, Nucleotides and Nucleic Acids

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS

: NUCLEOS NUCLEOT NUCL

: 23

: 12

: 1849

: 1864

: 16

: 1525-7770

DOI: https://doi.org/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 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.

Chemical sciences