A series of 2-O-trifluoromethylsulfonyl-D-mannopyranosides as precursors for concomitant 18F-labeling and glycosylation by click chemistry

A series of 'clickable' mannopyranosides bearing a triflate leaving group at C-2 position were synthesized and tested for their potential as F-18-labeling precursors. 3,4,6-Tri-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranosyl azide (2 beta) was the most convenient precursor for a site-specific and reliable click chemistry-based three-step, two-pot concomitant F-18-labeling and glycosylation of an alkyne-functionalized amino acid derivative. (C) 2009 Elsevier Ltd. All rights reserved.