(2S,3R,4S,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diyldimethanesulfonate

• 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: (2S,3R,4S,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diyldimethanesulfonate
• 英文别名: [(2S,3R,4S,5S)-5-methylsulfonyloxy-2,3,4,6-tetrakis(phenylmethoxy)hexyl] methanesulfonate
• 化学式: C₃₆H₄₂O₁₀S₂
• 分子量: 698.855
• InChiKey: PSRQUUMTYKKBPW-CLLHQPRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diyldimethanesulfonate 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 116.0h， 生成 米格鲁他
  参考文献：
  名称：

  Facile and stereo-controlled synthesis of 2-deoxynojirimycin, Miglustat and Miglitol

  摘要：

  A novel and facile synthesis of a series of the biologically significant iminosugar derivatives including 2-deoxynojirimycin, Miglustat and Miglitol is reported. The synthesis features a strategic double inversion mechanism for securing the desired stereochemistry at C5 position of such glucose-type carbohydrate mimetics, representing a practical and remarkable improvement on the previously reported method that suffers from the loss of the stereo-control during the reaction process. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.063
• 作为产物：
  描述：

  (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate 在 吡啶 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 (2S,3R,4S,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diyldimethanesulfonate
  参考文献：
  名称：

  Facile and stereo-controlled synthesis of 2-deoxynojirimycin, Miglustat and Miglitol

  摘要：

  A novel and facile synthesis of a series of the biologically significant iminosugar derivatives including 2-deoxynojirimycin, Miglustat and Miglitol is reported. The synthesis features a strategic double inversion mechanism for securing the desired stereochemistry at C5 position of such glucose-type carbohydrate mimetics, representing a practical and remarkable improvement on the previously reported method that suffers from the loss of the stereo-control during the reaction process. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.063

文献信息

• Facile and stereo-controlled synthesis of 2-deoxynojirimycin, Miglustat and Miglitol
  作者：Zhen-Xing Zhang、Baolin Wu、Bin Wang、Tie-Hai Li、Peng-Fei Zhang、Li-Na Guo、Wen-jun Wang、Wei Zhao、Peng George Wang

  DOI：10.1016/j.tetlet.2011.05.063

  日期：2011.7

  A novel and facile synthesis of a series of the biologically significant iminosugar derivatives including 2-deoxynojirimycin, Miglustat and Miglitol is reported. The synthesis features a strategic double inversion mechanism for securing the desired stereochemistry at C5 position of such glucose-type carbohydrate mimetics, representing a practical and remarkable improvement on the previously reported method that suffers from the loss of the stereo-control during the reaction process. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.