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Synthesis 1994; 1994(8): 823-826
DOI: 10.1055/s-1994-25582
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Synthesis of 3′-(N-Acetylpiperazino)-2′,3′-dideoxy-D-ribo-hexofuranosyl and -D-erythro-pentofuranosyl Thymine Nucleosides

Gorm Vang Petersen* , Jesper Platz, Claus Nielsen, Jesper Wengel
  • *Department of Chemistry, Odense University, DK-5230 Odense M, Denmark
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Publikationsdatum:
17. September 2002 (online)

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Michael-type addition of N-acetylpiperazine to the α,β-unsaturated hexose aldehyde 1 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave an anomeric mixture of 3-(N-acetylpiperazino)-2,3-di-deoxy-D-ribo-hexofuranoses, which was acetylated to give the tri-O-acetyl derivative 2. Reaction of 2 with silylated thymine 5 using trimethylsilyl trifluoromethanesulfonate as catalyst gave the hexofuranose nucleosides 6 and 7. The pure anomers were deprotected using a saturated solution of NH3 in dry MeOH affording 8 and 9. Conversion of 8 and 9 into the corresponding pentofuranose nucleosides 10 and 11 was accomplished by periodate oxidative cleavage and subsequent reduction.