(2R,3R,4S,5S,6R)-2-((2-fluorobenzylidene)amino)-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) | 1380444-82-5

• 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,5S,6R)-2-((2-fluorobenzylidene)amino)-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)
• CAS: 1380444-82-5
• 化学式: C₃₃H₄₈FNO₉
• 分子量: 621.744
• InChiKey: WGOXITKJFAQGPD-ZLOLNMDISA-N

物化性质

• 沸点：
  616.4±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  126.79
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  吲哚 、 (2R,3R,4S,5S,6R)-2-((2-fluorobenzylidene)amino)-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) 在 四氯化锡 、 四丁基碘化铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以93%的产率得到N-[indol-3-yl-(2-fluorophenyl)methyl]-(2,3,4,6-tetra-O-pivaloyl-β-D-galactosyl)amine
  参考文献：
  名称：

  Asymmetric aza-Friedel–Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

  摘要：

  The diastereoselective formation of beta-N-glycosidically linked 3-indolyl methanamine derivatives 5 has been achieved with high yield via an aza-Friedel-Crafts reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and SnCl4 combining TBAI as catalyst in DCM at -50 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.115
• 作为产物：
  描述：

  2,3,4,6-四-O-叔戊酰基-beta-D-吡喃半乳糖胺 、 2-氟苯甲醛 在 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 生成 (2R,3R,4S,5S,6R)-2-((2-fluorobenzylidene)amino)-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Asymmetric aza-Friedel–Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

  摘要：

  The diastereoselective formation of beta-N-glycosidically linked 3-indolyl methanamine derivatives 5 has been achieved with high yield via an aza-Friedel-Crafts reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and SnCl4 combining TBAI as catalyst in DCM at -50 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.115