Synthesis and conformation of 1‐(3′‐C‐methyl‐2′‐deoxy‐β‐D‐xylofuranosyl)uracil and 9‐(3′‐C‐methyl‐2′‐deoxy‐β‐D‐xylofuranosyl)adenine; two novel sugar‐methylated nucleoside analogues
- 1 January 1988
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 107 (4) , 343-346
- https://doi.org/10.1002/recl.19881070408
Abstract
The preparation and high‐resolution 1H NMR conformational analysis of the two novel nucleoside analogues, 1‐(3′‐C‐methyl‐2′‐deoxy‐β‐D‐xylofuranosyl)uracil (compound 1) and 9‐(3′‐C‐methyl‐2′‐deoxy‐β‐D‐xylofuranosyl)adenine (compound 2), are described. Compounds 1 and 2 show a pronounced preference for the north conformation of the sugar ring. The north conformation corresponds with a sterically favoured equatorial location of the methyl group. The C4′ ‐ C5′ conformation in 1 and 2 is predominantly γt (trans orientation of O5′ and C3′). The configuration at C3′ in 1 and 2 was corroborated via a one‐dimensional NOE experiment. The structure of compound 1 (originally assigned as having the C3′‐methyl group on the β‐face of the furanosyl moiety) is revised on the basis of these data.Keywords
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