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Synthesis of the First Selenium‐Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors
Author(s) -
Maza Susana,
López Óscar,
Martos Sergio,
Maya Inés,
FernándezBolaños José G.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900793
Subject(s) - chemistry , diselenide , imidazole , imidazolidine , acetylation , glycosidic bond , stereochemistry , anomer , chemoselectivity , selenium , organic chemistry , catalysis , biochemistry , gene , enzyme
We report the synthesis of acyclic and spiranic imidazole‐derived C ‐selenonucleosides. 5‐Hydroxy‐4‐tetrahydroxybutyl imidazolidine‐2‐selones, a novel class of acyclic selenonucleosides, were transformed into (tetrahydroxybutylimidazol‐2‐yl)diselenide, by acetylation and chemoselective N ‐deacetylation with methanolic imidazole. Furthermore, the synthesis of a new class of conformationally restricted arabino ‐configured spironucleosides containing an imidazolidine‐2‐selone unit around the glycosidic bond was achieved, starting from N ‐fructosamines, via 4‐hydroxy‐4‐tetrahydoxybutyl‐imidazolidine‐2‐selones as the key intermediates. Acetylation–deacetylation of these intermediates gave access to stable aromatic imidazoline‐2‐selones.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)