Concise Synthesis of the Anti-HIV Nucleoside EFdA

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  • KAGEYAMA Masayuki
    Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
  • MIYAGI Takuho
    Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
  • YOSHIDA Mayumi
    Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
  • NAGASAWA Tomohiro
    Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
  • OHRUI Hiroshi
    Yokohama College of Pharmacy Yokohama College of Pharmacy
  • KUWAHARA Shigefumi
    Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University

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EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine), a nucleoside reverse transcriptase inhibitor with extremely potent anti-HIV activity, was concisely synthesized from (R)-glyceraldehyde acetonide in an 18% overall yield by a 12-step sequence involving highly diastereoselective ethynylation of an α-alkoxy ketone intermediate. The present synthesis is superior, both in overall yield and in the number of steps, to the previous one which required 18 steps from an expensive starting material and resulted in a modest overall yield of 2.5%.

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