Open AccessHighly -selective, N-iodosuccinimide-mediated nucleosidation to bicyclo- and tricyclo-nucleosides
Author(s) -
Samuel Luisier,
Peter Šilhár,
Christian J. Leumann
Publication year - 2008
Publication title -
nucleic acids symposium series
Language(s) - English
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/nrn294
Subject(s) - bicyclic molecule , pyrimidine , purine , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , enzyme
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.
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