Synthesis of 3'-O-(2-aminoethyl)-2'-deoxyuridines

Acta Chem Scand (Cph). 1995 Aug;49(8):609-14. doi: 10.3891/acta.chem.scand.49-0609.

Abstract

Methyl 2-deoxy-3-O-[2-(formylamino)ethyl]-5-O-trityl-D-erythro- pentofuranoside (4) was obtained in a 3-O alkylation reaction by treatment with 2-chloroethylamine in DMF. Compound 4 afforded alpha nucleosides as the main products when condensed with uracils under the Vorbrüggen conditions. The nucleosides were deblocked by treatment with 80% acetic acid and subsequently with sodium methoxide in methanol.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Cell Survival / drug effects
  • Cells, Cultured
  • Chlorocebus aethiops
  • Deoxyuridine / analogs & derivatives*
  • Deoxyuridine / chemical synthesis*
  • Deoxyuridine / pharmacology
  • HIV-1 / drug effects
  • Haplorhini
  • Vero Cells / drug effects

Substances

  • Antiviral Agents
  • Deoxyuridine