Synthese von 7‐Desaza‐2′,3′‐didesoxyguanosin durch Desoxygenierung seines 2′‐Desoxy‐β‐D‐ribofuranosids
- 14 March 1988
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1988 (3) , 215-219
- https://doi.org/10.1002/jlac.198819880306
Abstract
7‐Desaza‐2′,3′‐didesoxyguanosin (4) wurde ausgehend von 7‐Desaza‐2′‐desoxyguanosin (1) durch Barton‐Desoxygenierung dargestellt. Der Schutz der 5′‐Hydroxygruppe erfolgte durch den 4,4′‐Dimethoxytriphenylmethyl‐Rest, der der 2‐Aminofunktion ent‐weder durch die Dimethylaminomethylengruppe oder ebenfalls durch den 4,4′‐Dimethoxytriphenylmethyl‐Rest. Die Zuordnung der 1H‐ und 13C‐NMR‐Signale des 2′,3′‐Didesoxy‐β‐D‐glycero‐pentofuranosyl‐Restes wurde bei 4 mittels 2D‐NMR‐Spektroskopie vorgenommen. Das Didesoxynucleosid 4 zeichnet sich gegenüber 2′,3′‐Didesoxyguanosin durch eine extrem hydrolysestabile N‐glycosylische Bindung aus.Keywords
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