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Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill. 2016
Olga Eguaogie, and
Leonie A Cooke, and
Patricia M L Martin, and
Francesco Ravalico, and
Louis P Conway, and
David R W Hodgson, and
Christopher J Law, and
Joseph S Vyle
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK. j.vyle@qub.ac.uk.
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.
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