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

Research output: Contribution to journalArticle

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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

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Organophosphonates
Nucleosides
Thymidine
5'-deoxythymidine
selenocyanic acid
benzyl selenocyanate
2,6-lutidine

Keywords

  • Michaelis-Arbuzov
  • Phosphoroselenolate
  • nucleotides
  • Selenocyanate

Cite this

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title = "Synthesis of nucleoside phosphoroselenolates via the efficient Michaelis-Arbuzov reaction of selenocyanates",
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.",
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Synthesis of nucleoside phosphoroselenolates via the efficient Michaelis-Arbuzov reaction of selenocyanates. / Eguaogie, Olga; Conlon, Patrick F.; Vyle, Joseph S.

In: Tetrahedron Letters, Vol. 57, No. 45, 09.11.2016, p. 5000-5002.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of nucleoside phosphoroselenolates via the efficient Michaelis-Arbuzov reaction of selenocyanates

AU - Eguaogie, Olga

AU - Conlon, Patrick F.

AU - Vyle, Joseph S.

PY - 2016/11/9

Y1 - 2016/11/9

N2 - 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.

AB - 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.

KW - Michaelis-Arbuzov

KW - Phosphoroselenolate

KW - nucleotides

KW - Selenocyanate

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DO - 10.1016/j.tetlet.2016.09.096

M3 - Article

VL - 57

SP - 5000

EP - 5002

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JF - Tetrahedron Letters

SN - 0040-4039

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