Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis and Antiviral Activity of $2^1$-Fluorohexopyranosyl Nucleosides

  • Jeong, Lak-Shin (College of Pharmacy, Ewha Womans University) ;
  • Lee, Jong-Eun (College of Pharmacy, Ewha Womans University) ;
  • Kim, Hea-Ok (Department of Industrial Safety and Hygiene, Kyungin Womens College) ;
  • Chun, Moon-Woo (College of Pharmacy, Seoul National University)
  • Published : 1998.06.01
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Abstract

$2^1$-Fluorohexopyranosyl nucleosides 1a and 1b which contained a bioisosteric double bond and a fluorine were synthesized in 12 steps, starting from D-galactose. During diethylaminosulfur trifluoride (DAST) fluorination, retention of stereochemistry was observed through the participation of methoxy or chloro group at the 6-posiition of the purine base. The final nucleosides 1a and 1b were found to be inactive against HIV-1 and HSV-1,2.

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