Practical synthesis of 1′-substituted Tubercidin C-nucleoside analogs

Several 1'-substituted analogs of Tubercidin C-nucleosides were prepared using a highly convergent synthesis. Good to high diastereoselectivity was achieved using a variety of nucleophiles targeting the 1'-position. The source for this stereoselectivity is herein proposed. It is thought to be attributed to a temperature-dependent chelation of the incoming nucleophile to either the 2'- or 3'-benzyloxy ether of the ribose core. (C) 2011 Elsevier Ltd. All rights reserved.