Synthesis of thietane nucleoside with an anomeric hydroxymethyl group

Thietane nucleoside 5 with an anomeric hydroxymethyl group was synthesized via the Pummerer reaction. The stereochemistry of the sulfoxide and the nature of the protecting group had no significant effect on the yield of the reaction. When a hypervalent iodine reagent was used, sulfide 16 with O-benzoyl protecting groups gave the ring-expanded nucleoside 21. Unfortunately, synthesized compound 6 did not exhibit anti-HSV activity. (C) 2010 Elsevier Ltd. All rights reserved.