Reactions of 2',3'-Di-O-mesyl-lyxo-uridine with secondary amines: first report on the one-pot conversion of mesylated nucleosides to enaminonucleosides and the crystal structure of α-enamine

Sakthivel, Kandasamy ; Pathak, Tanmaya ; Suresh, Cheravakkattu G. (1994) Reactions of 2',3'-Di-O-mesyl-lyxo-uridine with secondary amines: first report on the one-pot conversion of mesylated nucleosides to enaminonucleosides and the crystal structure of α-enamine Tetrahedron, 50 (46). pp. 13251-13260. 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(01)89333-9

Abstract

2',3'-Di-O-mesyl-5'-O-trityl-lyxo-uridine 1 reacted with secondary amines to produce enaminonucleosides 2a-d and 3a-d. Intermediacy of 2'-ketouridine was essential for the anomerisation and enamine formation to take place. The structure of the β-enamine was established unambiguously by analysing the hydrolysed product and that of α-enamine was proved with the help of crystal structure analysis.

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