Bulletin of the Korean Chemical Society

  • 제25권2호
  • /
  • Pages.221-225
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  • 2004
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Enantiomeric Synthesis of Novel Apiosyl Nucleosides as Potential Antiviral Agents

  • 발행 : 2004.02.20
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초록

A series of 2',3'-dideoxy-3'-fluoro-D-apiosyl nucleosides 15, 16, 17 and 18 were synthesized enantiomerically with L-Gulonic- ${\gamma}$-lactone as the starting material. The reduction of butenolide 1 with DIBAL-H followed by the Luche procedure afforded the allylic alcohol 2. Ozonolysis and the reduction of compound 4 induced the cyclized lactol, which was acetylated to give the acetate 7. Condensation of the acetate 7 with silylated pyrimidine ($N^4$-benzoyl cytosine) and a purine base (6-chloropurine) under Vorbruggen conditions and deblocking afforded a series of fluorinated apiosyl nucleosides.

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참고문헌

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피인용 문헌

  1. Enantiomeric Synthesis of Novel Apiosyl Nucleosides as Potential Antiviral Agents. vol.35, pp.32, 2004, https://doi.org/10.1002/chin.200432236
  2. C-C Bond Formation at C-5 Position of Dimethyluracil Derivatives Using SmI2 vol.25, pp.11, 2004, https://doi.org/10.5012/bkcs.2004.25.11.1631
  3. Nucleosides with Transposed Base or 4′-Hydroxymethyl Moieties and Their Corresponding Oligonucleotides vol.115, pp.24, 2015, https://doi.org/10.1021/acs.chemrev.5b00545