1,5-imino-1,5,6-trideoxy-N-benzhydryl-2,3,4-tri-O-benzyl-D-glucitol | 195380-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-imino-1,5,6-trideoxy-N-benzhydryl-2,3,4-tri-O-benzyl-D-glucitol
• 英文别名: (2R,3R,4R,5S)-1-benzhydryl-2-methyl-3,4,5-tris(phenylmethoxy)piperidine
• CAS: 195380-93-9
• 化学式: C₄₀H₄₁NO₃
• 分子量: 583.77
• InChiKey: JFBXSSFCESPSFM-DADYKTJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-imino-1,5,6-trideoxy-N-benzhydryl-2,3,4-tri-O-benzyl-D-glucitol 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以87%的产率得到1,5,6-trideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  A Stereoselective Synthesis of 1,6-Dideoxynojirimycin by Double-Reductive Amination of Dicarbonyl Sugar

  摘要：

  DOI：

  10.1021/jo970826s
• 作为产物：
  描述：

  (3R,4S,5S)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran 在 lanthanum(III) chloride 、 sodium cyanoborohydride 、 sodium iodide 、 苯甲醇 作用下， 以 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 10.0h， 生成 1,5-imino-1,5,6-trideoxy-N-benzhydryl-2,3,4-tri-O-benzyl-D-glucitol
  参考文献：
  名称：

  LaCl3·7H2O/NaI/benzyl alcohol: a novel reagent system for regioselective hydration of glycals: application in the synthesis of 1,6-dideoxynojirimycin

  摘要：

  Glycals can be readily hydrated using the LaCl3.7H(2)O/NaI/PhCH2OH reagent system. In one case, having an exo methylene group, such hydration gives an intermediate which is readily converted into 1,6-dideoxynojirimycin, a potential enzyme inhibitor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01175-4

文献信息

• LaCl3·7H2O/NaI/benzyl alcohol: a novel reagent system for regioselective hydration of glycals: application in the synthesis of 1,6-dideoxynojirimycin
  作者：Shikha Rani、Aditi Agarwal、Yashwant D Vankar

  DOI：10.1016/s0040-4039(03)01175-4

  日期：2003.6

  Glycals can be readily hydrated using the LaCl3.7H(2)O/NaI/PhCH2OH reagent system. In one case, having an exo methylene group, such hydration gives an intermediate which is readily converted into 1,6-dideoxynojirimycin, a potential enzyme inhibitor. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A Stereoselective Synthesis of 1,6-Dideoxynojirimycin by Double-Reductive Amination of Dicarbonyl Sugar
  作者：Dilip D. Dhavale、Nabendu N. Saha、Vijaya N. Desai

  DOI：10.1021/jo970826s

  日期：1997.10.1