Issue 4, 2016

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
05 Oct 2015
Accepted
06 Nov 2015
First published
13 Nov 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 1201-1205

Author version available

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

O. Eguaogie, L. A. Cooke, P. M. L. Martin, F. Ravalico, L. P. Conway, D. R. W. Hodgson, C. J. Law and J. S. Vyle, Org. Biomol. Chem., 2016, 14, 1201 DOI: 10.1039/C5OB02061A

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