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Synthesis 1989; 1989(11): 829-832
DOI: 10.1055/s-1989-27403
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A Convenient Method for the Synthesis of L-3′-Amino-2′,3′-dideoxyuridines

Jesper Wengel* , Jesper Lau, Erik B. Pedersen
  • *Department of Chemistry, Odense University, DK-5230 Odense, Denmark
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Publication Date:
02 May 2002 (online)

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(2E,4R)-4-Acetoxy-5-hydroxy-2-pentenal (3) was synthesized from L-arabinose (1) via 3,4-di-O-acetyl-L-arabinal (2). Phthalimide as its 1,8-diazabicyclo[5.4.0]undec-7-ene salt was coupled to 3 at C-3 to give an anomeric mixture of 2,3-dideoxy-3-phthalimido-L-erythro-pentofuranose, which was acetylated to give the corresponding di-O-acetyl derivative 4. Reaction of 4 with silylated 2,4-dihydroxypyrimidines 5 in the presence of trimethylsilyl triflate as catalyst afforded the nucleosides 6 and 7. The pure β-anomers obtained by fractional crystallization were deprotected with 33% methylamine in absolute ethanol to give the corresponding L-3′-aminonucleosides 8. After fractional crystallization of 6c the pure α-anomer 7c was obtained from the mother liquid and deprotected to give the corresponding L-3′-aminonucleoside 9c.