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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 24, Number 9
BKCSDE 24(9)
September 20, 2003 

Synthesis and Antiviral Evaluation of Novel Acyclic Nucleosides
Joon Hee Hong, Ok Hyun Ko
Acyclic nucleosides, [3,3]-Sigmatropic rearrangement, Antiviral agents
A very short and concise synthetic route for a novel acyclic version of d4T is described. The required quaternary carbon was successfully installed using a [3,3]-sigmatropic rearrangement. The condensation of the mesylates 16-18 with an adenine base under standard nucleophilic substitution conditions (K2CO3, 18-Crown- 6, DMF) in addition to deblocking afforded the target acyclic nucleosides 22-24. In addition, the antiviral evaluations against various viruses were performed.
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