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Synthesis, NMR studies and theoretical calculations of novel 3-spiro-branched ribofuranoses

AuthorsCamarasa Rius, María José ; Jimeno, M. Luisa ; Pérez Pérez, María Jesús; Álvarez, Rosa; Velázquez, Sonsoles ; Lozano López, Ángel Emilio
KeywordsSpiro compounds
Issue Date1999
PublisherPergamon Press
CitationTetrahedron 55 : 12187-12200 (1999)
AbstractNovel spiro-branched sugar derivatives bearing a spiro-5'-(4'-amino-2'-oxazolone) or a spiro-5'-(4'- amino-l',2',3'-oxathiazole-2',2'-dioxide) tings at position-3 of the sugar moiety have been prepared. The synthesis has been achieved by a one-pot procedure from a conveniently protected sugar cyanohydrin derivative by reaction with chlorosulfonyl isocyanate or sulfamoyl chloride, respectively. The tautometic preference in solution of these novel 3-spiro sugars are described as derived from NMR spectroscopy. Also a comparative theoretical study, by ab-initio methods, of the steric and electronic properties of the spiro tings present in these sugar derivatives has been performed.
Publisher version (URL)http://bit.ly/l3yxiz
Appears in Collections:(CENQUIOR) Artículos
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