Vijayalakshmi N, Maitra Uday
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
J Org Chem. 2006 Jan 20;71(2):768-74. doi: 10.1021/jo052173i.
[reaction: see text] The high reactivity of the chloroacetyl group has been exploited for the synthesis of bile acid based first and second generation dendrons with multiple hydroxyl groups. The synthesis involves only a few steps and avoids the use of protecting groups for the terminal hydroxyl groups. These dendritic structures with facially amphiphilic bile acid backbones on the periphery were able to solubilize cresol red, a hydrophilic dye, in a nonpolar solvent. HPLC analysis of the dendrons suggests that hydrophobicity increases with increase in oligomer size, but in each generation, the dendrons with a higher degree of branching are less hydrophobic.
[反应：见正文] 氯乙酰基的高反应活性已被用于合成具有多个羟基的基于胆汁酸的第一代和第二代树枝状分子。合成仅涉及几个步骤，并且避免了对末端羟基使用保护基团。这些在外围具有表面两亲性胆汁酸主链的树枝状结构能够在非极性溶剂中溶解亲水性染料甲酚红。对树枝状分子的HPLC分析表明，疏水性随低聚物尺寸的增加而增加，但在每一代中，具有较高分支度的树枝状分子疏水性较低。
