Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill

Eguaogie, Olga; Cooke, Leonie A.; Martin, Patricia M.L.; Ravalico, Francesco; Conway, Louis P.; Hodgson, David R.W.; Law, Christopher J.; Vyle, Joseph S.

doi:10.1039/c5ob02061a

Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill

Eguaogie, Olga; Cooke, Leonie A.; Martin, Patricia M.L.; Ravalico, Francesco; Conway, Louis P.; Hodgson, David R.W.; Law, Christopher J.; Vyle, Joseph S.

Authors

Olga Eguaogie

Leonie A. Cooke

Patricia M.L. Martin

Francesco Ravalico

Louis P. Conway

Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor

Christopher J. Law

Joseph S. Vyle

Abstract

Michaelis–Arbuzov reactions of S-aryl disulfide derivatives of 3′-thiothymidine or 5′-thioadenosine with tris(trimethylsilyl) phosphite proceeded in high yields to the corresponding phosphorothiolate monoesters. Subsequent hydrolytic desilylation and phosphate coupling were effected in one-pot using liquid-assisted grinding in a vibration ball mill. Novel 3′,5′- and 5′,5′-pyrophosphorothiolate-linked dinucleoside cap analogues were thereby prepared.

Citation

Eguaogie, O., Cooke, L. A., Martin, P. M., Ravalico, F., Conway, L. P., Hodgson, D. R., …Vyle, J. S. (2016). Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill. Organic and Biomolecular Chemistry, 14(4), 1201-1205. https://doi.org/10.1039/c5ob02061a

Journal Article Type	Article
Acceptance Date	Nov 6, 2015
Online Publication Date	Nov 13, 2015
Publication Date	Jan 28, 2016
Deposit Date	Nov 9, 2015
Publicly Available Date	Nov 13, 2015
Journal	Organic and Biomolecular Chemistry
Print ISSN	1477-0520
Electronic ISSN	1477-0539
Publisher	Royal Society of Chemistry
Peer Reviewed	Peer Reviewed
Volume	14
Issue	4
Pages	1201-1205
DOI	https://doi.org/10.1039/c5ob02061a