Synthesis of azide-alkyne fragments for “Click” chemical applications. Part 2. Formation of oligomers from orthogonally protected chiral trialkylsilylhomopropargyl …

OD Montagnat, G Lessene…

Index: Montagnat, Oliver D.; Lessene, Guillaume; Hughes, Andrew B. Journal of Organic Chemistry, 2010 , vol. 75, # 2 p. 390 - 398

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Citation Number: 23

Abstract

A small library of chiral, β3-substituted homopropargyl alcohols and chiral β3-substituted trimethylsilylhomopropargyl azides were generated starting from natural l-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1, 3-dipolar cycloaddition, to provide chiral oligomeric 1, 4-disubstituted-1, 2, 3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally ...