叠氮-炔片段的合成用于“点击”化学应用。第 2 部分。通过正交保护的手性三烷基硅基偕丙基叠氮化物和偕丙基醇形成低聚物。

Synthesis of azide-alkyne fragments for "click" chemical applications. Part 2. Formation of oligomers from orthogonally protected chiral trialkylsilylhomopropargyl azides and homopropargyl alcohols.

机构信息

Department of Chemistry, La Trobe University, Melbourne, Victoria 3086, Australia.

出版信息

J Org Chem. 2010 Jan 15;75(2):390-8. doi: 10.1021/jo9021887.

PMID:20000729

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.

摘要

从天然 L-氨基酸出发，生成了一个小的手性、β(3)-取代的偕丙炔醇和手性β(3)-取代的三甲基硅基偕丙炔基叠氮化物库。然后，通过 Huisgen 1,3-偶极环加成反应，将游离的炔烃和叠氮化物偶联，得到手性寡聚 1,4-二取代-1,2,3-三唑，作为潜在的肽模拟化合物。这项工作是对以前的合成的外消旋的、正交保护的 1,4-二取代-1,2,3-三唑的扩展，该化合物是由相应的α-取代的丙炔醇和α-取代的三烷基硅基丙炔基叠氮化物得到的。