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Synthesis 2006(14): 2343-2348
DOI: 10.1055/s-2006-942438
DOI: 10.1055/s-2006-942438
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of a Thymidine-Derived Acylsilane: A New Synthetic Intermediate towards Thymidine Analogues
Weitere Informationen
Received
10 March 2006
Publikationsdatum:
26. Juni 2006 (online)
Publikationsverlauf
Publikationsdatum:
26. Juni 2006 (online)
Abstract
An efficient procedure was established to synthesize a thymidine analogue bearing an acylsilane function at the 5′-position, starting from thymidine in four steps and 58% overall yield. This compound proved to be a valuable intermediate for the synthesis of various nucleoside analogues with a one-carbon chain elongation at the 5′-position and a useful compound towards the construction of modified oligonucleotides.
Key words
acylsilanes - thymidine - nucleoside analogues - photo-Brook rearrangement - oxidation
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References
Bercier, A.; Plantier-Royon, R.; Portella, C. unpublished results.
16We reacted compound 3 (1 equiv) with 2-lithio-1,3-dithiane (4 equiv) for 6 h at -30 °C in THF. A major compound was isolated and was identified as a dimeric analogue of the expected 5′-dithianyl-thymidine derivative.