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

Olga Eguaogie; Patrick F. Conlon; Joseph S. Vyle

doi:10.1016/j.tetlet.2016.09.096

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

Olga Eguaogie
, Patrick F. Conlon
, Joseph S. Vyle

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

443 Downloads (Pure)

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 language	English
Pages (from-to)	5000-5002
Number of pages	3
Journal	Tetrahedron Letters
Volume	57
Issue number	45
Early online date	29 Sept 2016
DOIs	https://doi.org/10.1016/j.tetlet.2016.09.096
Publication status	Published - 09 Nov 2016

Keywords

Michaelis-Arbuzov
Phosphoroselenolate
nucleotides
Selenocyanate

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10.1016/j.tetlet.2016.09.096Licence: Unspecified

Synthesis of nucleoside phosphoroselenolates via the efficient MichaelisArbuzov reaction of selenocyanates
© 2016 Elsevier Ltd. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/,which permits distribution and reproduction for non-commercial purposes, provided the author and source are cited.
Accepted author manuscript, 94.2 KBLicence: CC BY-NC-ND

http://www.sciencedirect.com/science/article/pii/S0040403916312898Licence: Unspecified

Novel approaches to the synthesis of selenium modified nucleosides, nucleotides and nucleic acids
Conlon, P. (Author), Vyle, J. (Supervisor) & Hale, K. (Supervisor), Jul 2021
Student thesis: Doctoral Thesis › Doctor of Philosophy

Joseph Samuel Vyle
- j.vylequb.acuk
- School of Chemistry and Chemical Engineering - Lecturer
- Organic Synthesis and Chemical Biology
Person: Academic

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill
Eguaogie, O., Conlon, P. F., Ravalico, F., Sweet, J., Elder, T. B., Conway, L. P., Lennon, M. E., Hodgson, D. R. W. & Vyle, J. S., 13 Jan 2017, In: Beilstein Journal of Organic Chemistry. 13, p. 87–92 6 p.
Research output: Contribution to journal › Article › peer-review

Open Access
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410 Downloads (Pure)

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.",

keywords = "Michaelis-Arbuzov, Phosphoroselenolate, nucleotides, Selenocyanate",

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journal = "Tetrahedron Letters",

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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

U2 - 10.1016/j.tetlet.2016.09.096

DO - 10.1016/j.tetlet.2016.09.096

M3 - Article

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VL - 57

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EP - 5002

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

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

Abstract

Keywords

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Student theses

Novel approaches to the synthesis of selenium modified nucleosides, nucleotides and nucleic acids

Profiles

Joseph Samuel Vyle

Research output

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill

Cite this