289906-59-8Relevant academic research and scientific papers
The first direct ammonolysis of 2-thiouracil nucleosides to 2- thiocytosine nucleosides
Strekowski, Lucjan,Abdou, Ibrahim M.,Attia, Adel M.E.,Patterson, Steven E.
, p. 4757 - 4761 (2000)
Sugar-peracetylated 1-(β-D-glucopyranosyl)-, 1-(β-D-galactopyranosyl)- , and 1-(β-D-xylopyranosyl)-6-aryl-5-cyano-2-thiouracils 2-4 and the corresponding 1-pyranosyl-2-(pyranosylthio)pyrimidines 5-7 undergo efficient ammonolysis (NH3/MeOH, 0→23
A facile synthesis of 6-aryl-5-cyano-1-(β-D-pyranosyl or β-D-furanosyl)-2-thiocytosines
Abdou, Ibrahim M,Strekowski, Lucjan
, p. 8631 - 8636 (2007/10/03)
The treatment of a piperidinium salt of 6-aryl-5-cyano-2-thiouracil with an O-peracetyl-α-D-pyranosyl bromide produces a mixture of N1-(β-D-pyranosyl)-2-thiouracil and its N1,S2-disubstituted analog. By contrast, the reaction of a silyl derivative of the 2-thiouracil with an O-peracetyl-β-D-pyranose furnishes the mononucleoside selectively. Both the mononucleoside/dinucleoside mixture and pure mononucleoside undergo ammonolysis under mild conditions to give the β-D-nucleoside of 6-aryl-5-cyano-2-thiocytosine. The silyl method also provides an easy access to β-D-ribosyl nucleosides. (C) 2000 Elsevier Science Ltd.
