(E)-methyl 4-(β-D-galactopyranosyl)but-2-enoate | 1071472-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-methyl 4-(β-D-galactopyranosyl)but-2-enoate
• 英文别名: (E)-Methyl 4-(beta-D-galactopyranosyl)-but-2-enoate；methyl (E)-4-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]but-2-enoate
• CAS: 1071472-88-2
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: KCBPFVCIEDLNTD-FVGWVXRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-but-2-enoate 在 甲醇 、 sodium methylate 作用下， 以100%的产率得到(E)-methyl 4-(β-D-galactopyranosyl)but-2-enoate
  参考文献：
  名称：

  使用多米诺·赫克反应/内酯化工艺催化合成新型4- C-糖基香豆素

  摘要：

  使用多米诺·赫克反应/内酯化过程实现了新型4-连接的C-糖基香豆素的催化合成。在Heck条件下，使用一组芳基碘化物，由4-糖基-丁-2-烯酸甲酯制备3-糖基肉桂酸甲酯。这种新方法的直接应用是针对半乳糖凝集素-1和-3的初步血凝抑制试验。C-半乳糖苷30对半乳凝素1的IC 50为313μM。

  DOI：

  10.1016/j.tetlet.2009.04.134

文献信息

• Synthesis of stable and selective inhibitors of human galectins-1 and -3
  作者：Denis Giguère、Marc-André Bonin、Philipe Cloutier、Ramesh Patnam、Christian St-Pierre、Sachiko Sato、René Roy

  DOI：10.1016/j.bmc.2008.06.044

  日期：2008.8

  The syntheses of glycolytically stable galactosides and lactosides have been made toward the selective inhibition of human galectins-1 and -3. Transition metal-catalyzed cross-coupling reactions were used to create carbon-carbon bond formation (Sonogashira, Suzuki, Heck, Glaser). Additionally, Hantzsch condensation was used to create novel 2-aminothiazoles which reacted with a panel of acylating and sulfonylating reagents. Moreover, dimeric galactosides and lactosides bearing triazoles, regiospeci.cally prepared using copper-catalyzed Huisgen azide-alkyne [1,3]-dipolar cycloaddition, provided efficient galectins-1 and -3 inhibitors. Best monovalent inhibitor among the tested series was (E)-methyl 2-phenyl-4-(beta-D-galactopyranosyl)-but-2-enoate 15 with inhibitory potency of 313 mu M against galectin-1 and best dimers were bis-lactoside 68 and 75 having both inhibitory properties of 160 mu M against Galectin-3. (c) 2008 Elsevier Ltd. All rights reserved..
• Catalytic synthesis of novel 4-C-glycosyl coumarins using a domino Heck reaction/lactonization process
  作者：Denis Giguère、Ramesh Patnam、Juan M. Juarez-Ruiz、Mathieu Neault、René Roy

  DOI：10.1016/j.tetlet.2009.04.134

  日期：2009.7

  A catalytic synthesis of novel 4-linked C-glycosyl coumarins was achieved using a domino Heck reaction/lactonization process. Methyl 3-glycosyl cinnamates were prepared from methyl 4-glycosyl-but-2-enoates using a panel of aryl iodides under Heck conditions. A direct application of this new methodology was made toward preliminary hemagglutination inhibition assays against galectins-1 and -3. C-Galactoside

  使用多米诺·赫克反应/内酯化过程实现了新型4-连接的C-糖基香豆素的催化合成。在Heck条件下，使用一组芳基碘化物，由4-糖基-丁-2-烯酸甲酯制备3-糖基肉桂酸甲酯。这种新方法的直接应用是针对半乳糖凝集素-1和-3的初步血凝抑制试验。C-半乳糖苷30对半乳凝素1的IC 50为313μM。