Synthesis of Azide-Alkyne Fragments for "Click" Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols
- Author(s)
- Montagnat, OD; Lessene, G; Hughes, AB;
- Details
- Publication Year 2010-01-15,Volume 75,Issue #2,Page 390-398
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Publication Type
- Journal Article
- Abstract
- A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-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 protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.
- Publisher
- AMER CHEMICAL SOC
- Keywords
- GLUTAMIC-ACID; ESTERS; FOLDAMERS
- Publisher's Version
- https://doi.org/10.1021/jo9021887
- Terms of Use/Rights Notice
- Refer to copyright notice on published article.
Creation Date: 2010-01-15 12:00:00