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.

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