One-pot deoxygenative conversion of a ribonucleoside to enaminonucleosides involving 1,2-hydride shift rearrangement

Sakthivel, Kandasamy ; Pathak, Tanmaya (1996) One-pot deoxygenative conversion of a ribonucleoside to enaminonucleosides involving 1,2-hydride shift rearrangement Tetrahedron, 52 (13). pp. 4877-4882. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/0...

Related URL: http://dx.doi.org/10.1016/0040-4020(96)00159-7

Abstract

5'-O-Trityl-3'-O-mesyluridine on reaction with secondary ramines produced 1-(2,3-dideoxy-2-N-dialkylamino-5-O-trityl- D-glycero-pent-2-enofuranosyl) uracil involving 1,2-hydride shift. The reaction proceeded through the formation of 2′-ketouridine in situ which was evident from the formation of both the α- and β- anomers of the enaminonucleosides.

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