N,N'-bis-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-2,2'-bipyridine-3,3'-carboxamide | 1163299-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N'-bis-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-2,2'-bipyridine-3,3'-carboxamide
• 英文别名: N-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl]-2-[3-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methylcarbamoyl]pyridin-2-yl]pyridine-3-carboxamide
• CAS: 1163299-46-4
• 化学式: C₃₆H₄₆N₄O₁₂
• 分子量: 726.781
• InChiKey: NTIWAZLFDSFVGZ-XAEFHZSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  52
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-galactopyranose 、 2,2'-联吡啶-3,3'-二羧酸 在 三乙基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以26%的产率得到N,N'-bis-(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-2,2'-bipyridine-3,3'-carboxamide
  参考文献：
  名称：

  2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination

  摘要：

  A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2'-bipyridine-3,3'-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.050

文献信息

• 2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination
  作者：Aurélie Assalit、Thierry Billard、Stéphane Chambert、Bernard R. Langlois、Yves Queneau、Diane Coe

  DOI：10.1016/j.tetasy.2009.02.050

  日期：2009.3

  A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2'-bipyridine-3,3'-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.