[(2R,3R,4S,5R,6R)-3,4,5-tris(2-methylprop-2-enoyloxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 2-methylprop-2-enoate | 1198417-98-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-tris(2-methylprop-2-enoyloxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 2-methylprop-2-enoate
• CAS: 1198417-98-9
• 化学式: C₂₄H₂₈Cl₃NO₁₀
• 分子量: 596.846
• InChiKey: CIWISAIAFRJKJQ-XBJPRQPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-tris(2-methylprop-2-enoyloxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 2-methylprop-2-enoate 、 苯酚 在 [双(三氟甲磺酰基)氨基]三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以41%的产率得到[(2R,3R,4S,5R,6S)-3,4,5-tris(2-methylprop-2-enoyloxy)-6-phenoxyoxan-2-yl]methyl 2-methylprop-2-enoate
  参考文献：
  名称：

  TMSNTf 2促进的高化学和立体选择性糖基化的甲基丙烯酸酯化的O-糖基三氯乙酰亚氨酸盐试剂

  摘要：

  TMSNTf 2已有效地用作涉及过甲基丙烯酸酯化Schmidt试剂的糖苷化反应的促进剂。尽管已知TMSNTf 2是C O双键的强大活化剂，但我们发现，即使存在过甲基丙烯酸O-糖基三氯乙酰亚氨酸酯底物的过量C O基，该试剂也可以选择性活化C N双键。糖苷以中等至合理的产率合成，具有出色的整体β-立体选择性。

  DOI：

  10.1016/j.tet.2010.02.068
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-2-hydroxy-6-((methacryloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2-methylacrylate) 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-tris(2-methylprop-2-enoyloxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 2-methylprop-2-enoate
  参考文献：
  名称：

  Permethacrylated carbohydrates: synthesis and reactivity in glycosidation reaction

  摘要：

  The synthesis of various permethacrylated mono- and disaccharides in acceptable yields is reported. The reactivity of these unusual polymerizable compounds has been investigated in diverse glycosidation reaction conditions. New original polymerizable donor sugars have been prepared successfully in good to excellent yields. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.083

文献信息

• Permethacrylated carbohydrates: synthesis and reactivity in glycosidation reaction
  作者：Christelle Zandanel、Charles Mioskowski、Rachid Baati、Alain Wagner

  DOI：10.1016/j.tet.2009.08.083

  日期：2009.11

  The synthesis of various permethacrylated mono- and disaccharides in acceptable yields is reported. The reactivity of these unusual polymerizable compounds has been investigated in diverse glycosidation reaction conditions. New original polymerizable donor sugars have been prepared successfully in good to excellent yields. (c) 2009 Elsevier Ltd. All rights reserved.
• Highly chemo- and stereoselective glycosidation of permethacrylated O-glycosyl trichloroacetimidate reagents promoted by TMSNTf2
  作者：Christelle Zandanel、Laure Dehuyser、Alain Wagner、Rachid Baati

  DOI：10.1016/j.tet.2010.02.068

  日期：2010.5

  TMSNTf2 has been used efficiently as a promoter in glycosidation reaction involving permethacrylated Schmidt reagents. While TMSNTf2 is known to be a powerful activator for CO double bonds, we have discovered that this reagent can activate CN double bond selectively, even in the presence of excess CO groups of permethacrylated O-glycosyl trichloroacetimidate substrates. Glycosides are synthesized in

  TMSNTf 2已有效地用作涉及过甲基丙烯酸酯化Schmidt试剂的糖苷化反应的促进剂。尽管已知TMSNTf 2是C O双键的强大活化剂，但我们发现，即使存在过甲基丙烯酸O-糖基三氯乙酰亚氨酸酯底物的过量C O基，该试剂也可以选择性活化C N双键。糖苷以中等至合理的产率合成，具有出色的整体β-立体选择性。