Thermal degradation of sugar-modified uridine N-oxides: olefination, oxazolidination and rearrangements

Bera, Sanjib ; Pathak, Tanmaya (1999) Thermal degradation of sugar-modified uridine N-oxides: olefination, oxazolidination and rearrangements Tetrahedron, 55 (45). pp. 13051-13062. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4020(99)00797-8

Abstract

The degradation pattern of the N-oxides of various tertiary aminouridines is established. The N-oxide of 3'-deoxy-3'-morpholino-arauridine generated double bonds in the carbohydrate moiety without much selectivity, whereas epimino uridine N-oxides generated only d4U. Oxazolidine derivatives were formed from the N-oxides of 3'-deoxy-3'-N-pyrrolidino/morpholino-2,2'-O-anhydrouridines and 3'-deoxy-3'-N-pyrrolidino/morpholino-2'-O-mesylarauridines. 2'-Deoxy-2'-N-pyrrolidino/morpholino-2'-O-mesylxylouridines produced rearranged products 3'-O-N-pyrrolidino/morpholino-2,2'-O-anhydrouridines.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Nucleosides; N-oxides; Elimination Reactions; Rearrangements
ID Code:104217
Deposited On:17 Mar 2017 06:58
Last Modified:17 Mar 2017 06:58

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