Synthesis of nucleoside phosphoroselenolates via the efficient Michaelis-Arbuzov reaction of selenocyanates

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Abstract

The Michaelis-Arbuzov reactions of benzylselenocyanate and 5′-deoxythymidine-5′-selenocyanate with thymidine H-phosphonate proceeded rapidly in the presence of a neutral silylating agent and 2,6-lutidine to give the corresponding Se-alkyl phosphoroselenolate triesters. Deprotection under mild conditions enabled the isolation of phosphoroselenolate diesters which were fully characterised.
Original languageEnglish
Pages (from-to)5000-5002
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number45
Early online date29 Sep 2016
DOIs
Publication statusPublished - 09 Nov 2016

Keywords

  • Michaelis-Arbuzov
  • Phosphoroselenolate
  • nucleotides
  • Selenocyanate

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