(2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate | 1316108-84-5

• 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,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate
• 英文别名: [(2S,3R,4R,5R)-5-hydroxy-2,3,4,6-tetrakis(phenylmethoxy)hexyl] 2,2-dimethylpropanoate
• CAS: 1316108-84-5
• 化学式: C₃₉H₄₆O₇
• 分子量: 626.79
• InChiKey: AJPBCPOGXJZUJF-LADGJGSJSA-N

物化性质

• 沸点：
  715.8±60.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate 在 吡啶 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 126.0h， 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：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate
  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