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Synthesis 1992; 1992(3): 319-322
DOI: 10.1055/s-1992-26100
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Synthesis of 2′,3′-Dideoxy-3′-piperidino- and 2′, 3′-Dideoxy-3′-pyrrolidino-D-ribo-hexofuranosyl Nucleosides from Tri-O-acetyl-D-glucal

Jesper Wengel* , Erik B. Pedersen, Bent Faber Vestergaard
  • *Department of Chemistry, Odense University, DK-5230 Odense M, Denmark
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Publication Date:
17 September 2002 (online)

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α,β-Unsaturated aldehyde 1 prepared from tri-O-acetyl-D-glucal was reacted with piperidine and pyrrolidine in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. This gave anomeric mixtures of 2′,3′-dideoxy-3′-piperidino- and 2′,3′ -dideoxy-3′-pyrrolidino-D-ribo-hexofuranoses, which were acetylated to give the corresponding tri-O-acetyl derivatives 2 and 3. Reaction of 2 and 3 with silylated 2,4-dihydroxypyrimidines 4 using trimethylsilyl trifluoromethanesulfonate as catalyst gave the nucleosides 5 and 6. The pure anomers were treated with 33% methylamine in ethanol to give the corresponding unprotected nucleosides 7 and 8.