Highly beta-selective, N-iodosuccinimide-mediated nucleosidation to bicyclo- and tricyclo-nucleosides.
The N-iodosuccinimide (NIS) induced nucleosidation of protected natural bases with bicyclo[3.3.0] sugar precursors was investigated. It was found that this method is particularly suited for the synthesis of N(1)-pyrimidine nucleosides and provides a selective entry into N(7)-purine nucleosides. This nucleosidation is beta-specific and is a valuable alternative to the Vorbrüggen method.
Luisier
Samuel
S
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Swizerland.
Silhar
Peter
P
Leumann
Christian J
CJ
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry*
D001643:Bridged Bicyclo Compounds; D006575:Heterocyclic Compounds, 3-Ring; D009705:Nucleosides; D013388:Succinimides; C008155:N-iodosuccinimide