N-(2-hydroxy-ethyl)-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin | 1221793-46-9

• 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: N-(2-hydroxy-ethyl)-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin
• 英文别名: 2-[(2R,3R,4R,5S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)piperidin-1-yl]ethanol
• CAS: 1221793-46-9
• 化学式: C₃₆H₄₁NO₅
• 分子量: 567.725
• InChiKey: RMELSKYSYAAZAJ-IYKITFJXSA-N

物化性质

• 沸点：
  679.7±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-ethyl)-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 20.0h， 生成 米格列醇
  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：

  (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 106.0h， 生成 N-(2-hydroxy-ethyl)-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin
  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

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF METABOLIC SYNDROME AND DIABETES<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT DU SYNDROME MÉTABOLIQUE ET DU DIABÈTE
  申请人：KANDULA MAHESH

  公开号：WO2014087307A3

  公开（公告）日：2014-07-31
• 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.