bis(5-deoxy-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) 2,2'-bipyridine-3,3'-dicarboxylate | 1163299-24-8

• 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(5-deoxy-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) 2,2'-bipyridine-3,3'-dicarboxylate
• 英文别名: [(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 2-[3-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxycarbonyl]pyridin-2-yl]pyridine-3-carboxylate
• CAS: 1163299-24-8
• 化学式: C₃₀H₃₆N₂O₁₂
• 分子量: 616.622
• InChiKey: IHPUEXZKKFVJPL-ZXPLGDEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2,2'-联吡啶-3,3'-二羧酸 、 甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 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26%的产率得到bis(5-deoxy-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-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
• 作为试剂：
  描述：

  环戊羧酸,2-羰基-,苯基甲基酯 在 bis(5-deoxy-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) 2,2'-bipyridine-3,3'-dicarboxylate 、 copper(II) bis(trifluoromethanesulfonate) 、 N-氟代双苯磺酰胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到benzyl 1-fluoro-2-oxocyclopentane-1-carboxylate
  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.