Synthesis of azide-alkyne fragments for 'click' chemical applications formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols
Oliver D Montagnat, Guillaume Lessene, Andrew B Hughes
Tetrahedron Letters | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2006
A series of orthogonally protected 1,4-disubstituted-1,2,3-triazoles were prepared from the corresponding alkynols and trialkylsilyl-propargyl azides via 1,3-dipolar cycloaddition. These cycloadducts were selectively deprotected and extended in a stepwise fashion via further 'click' reactions to form oligomeric peptidomimetic compounds. This methodology gives access to triazole-based peptidomimetics in a controlled fashion and lays the foundation for a fragment-based approach to drug discovery. © 2006 Elsevier Ltd. All rights reserved.