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KMID : 0043319980210030338
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Archives of Pharmacal Research
1998 Volume.21 No. 3 p.338 ~ p.343
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Synthesis and Antiviral Activity of 2[1]-Fluorohexopyranosyl Nucleosides
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Jeong Lak-Shin
Lee Jong-Eun
Kim Hea-Ok
Chun Moon-Woo
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Abstract
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-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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KEYWORD
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Bioisosteric, DAST fluorination, Antiviral, Retention of configuration
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