Tetrahedron

Synthesis and biological properties of a new series of 5-substituted-pyrimidine-L-nucleoside analogues

NB Westwood, RT Walker

Index: Westwood, Nigel B.; Walker, Richard T. Tetrahedron, 1998 , vol. 54, # 44 p. 13391 - 13404

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Citation Number: 24

Abstract

trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L- nucleoside analogues incorporating non-standard 5-substituted-pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl) uracil-pyrrolidine-L-nucleosides 23–26. ...