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Synthesis and Conformational Analysis of C-4′-Modified (2-Oxabicyclo[3.1.0]hexyl)pyrimidine Nucleosides

✍ Scribed by Julien Gagneron; Gilles Gosselin; Christophe Mathé

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
170 KB
Volume
2006
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

We report on the synthesis of hitherto unknown pyrimidine nucleoside analogues bearing the 2‐oxabicyclo[3.1.0]hexane scaffold (5, 6, 8, 13–17 and 19) with various modifications at the C‐4′ position including methylene, azido, and arabino‐like configuration. Conformational analysis on the nucleoside analogues 6, 14 and 17 indicates that the conformation of such C‐4′‐modified nucleoside analogues was restricted in the South‐East hemisphere of the pseudorotation cycle (between a ^0^T~1~ and a ^2^E conformation). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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