A facile synthesis of 6-aryl-5-cyano-1-(β-D-pyranosyl or β-D-furanosyl)-2-thiocytosines

[摘要] The treatment of a piperidinium salt of 6-aryl-5-cyano-2-thiouracil with an O-peracetyl-alpha -D-pyranosyl bromide produces a mixture of N1-(beta -D-pyranosyl)-2-thiouracil and its N1,S-2-disubstituted analog. By contrast, the reaction of a silyl derivative of the 2-thiouracil with an O-pcracetyl-beta -D-pyranose furnishes the mononucleoside selectively. Both the mononucleoside/dinucleoside mixture and pure mononucleoside undergo ammonolysis under mild conditions to give the P-D-nucleoside of 6-aryl-5-cyano-2-thiocytosine. The silyl method also provides an easy access to beta -D-ribosyl nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

[发布日期] 2000-10-27

[关键词] 6-aryl-5-cyano-2-thiouracils;ammonolysis;1-(beta-D-pyranosyl)-2-thiocytosines;1-(beta-D-furanosyl)-2-thiocytosines