From ortho-carbaborane-9-thiol towards new building blocks

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• 作者：René ; Frank ; Solveig Boehnke ; Almaz Aliev ; Evamarie Hey-Hawkins ; ^{hey@uni-leipzig.de}
• 关键词：Antitumor agents ; Boron neutron capture therapy ; Carboranes ; Carbaboranes ; Glycosides ; Thiols
• 刊名：Polyhedron
• 出版年：2012
• 期刊代码：87_02775387
• 类别：ch
• 出版时间：30 May, 2012
• 卷：39
• 期：1
• 页码：9-13
• 文件大小：352 K

摘要

The potential of 1,2-dicarba-closo-dodecaborane(12)-9-thiol, 9-HS-1,2-closo-C₂B₁₀H₁₁, for the design of novel building blocks is highlighted by two examples envisioned for incorporation into tumor-selective peptides for boron neutron capture therapy (BNCT). By employing a t-Bu protection strategy the synthesis of a bis-galactosyl-substituted ortho-carbaborane carboxylic acid was elaborated, and the procedure is suggested as a general approach towards carbaboranes with three substituents. Furthermore, a simple route to a tris(ortho-carbaborane) building block starting from pentaerythritol is illustrated. All compounds were synthesized in moderate to high yields and identified by ¹H, ¹¹B, and ¹³C NMR spectroscopy, IR spectroscopy, mass spectrometry, and in one case by X-ray crystallography.