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

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

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)
265 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)1201–1205
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number4
Early online date13 Nov 2015
DOIs
Publication statusPublished - 2016

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