bis(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) 2,2'-bipyridine-3,3'-dicarboxylate | 1163299-28-2

• 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: bis(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) 2,2'-bipyridine-3,3'-dicarboxylate
• 英文别名: [(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]methoxycarbonyl]pyridin-2-yl]pyridine-3-carboxylate
• CAS: 1163299-28-2
• 化学式: C₃₆H₄₄N₂O₁₄
• 分子量: 728.75
• InChiKey: AOFVRBVGPROEIV-XAEFHZSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  52
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  171
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  2,2'-联吡啶-3,3'-二羧酸 、 双丙酮半乳糖 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到bis(6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) 2,2'-bipyridine-3,3'-dicarboxylate
  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.