A1 Refereed original research article in a scientific journal
Effective anomerisation of 2 '-deoxyadenosine derivatives during disaccharide nucleoside synthesis
Authors: Gulyaeva IV, Neuvonen K, Lonnberg H, Rodionov AA, Shcheveleva EV, Bobkov GV, Efimtseva EV, Mikhailov SN
Publisher: TAYLOR & FRANCIS INC
Publication year: 2004
Journal: Nucleosides, Nucleotides and Nucleic Acids
Journal name in source: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Journal acronym: NUCLEOS NUCLEOT NUCL
Volume: 23
Issue: 12
First page : 1849
Last page: 1864
Number of pages: 16
ISSN: 1525-7770
DOI: https://doi.org/10.1081/NCN-200040627
Abstract
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.
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.
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