(2S,3R,4R,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol | 78136-16-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R,4R,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol
• 英文别名: 1,3,4,5-tetra-O-benzyl-L-iditol；1,3,4,5-Tetrakis-O-(phenylmethyl)-L-iditol；(2S,3R,4R,5S)-2,3,4,6-tetrakis(phenylmethoxy)hexane-1,5-diol
• CAS: 78136-16-0
• 化学式: C₃₄H₃₈O₆
• 分子量: 542.672
• InChiKey: MQOUZFJJURBWAX-PSWJWLENSA-N

物化性质

• 溶解度：
  溶于DCM、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol 在 吡啶 、 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 121.0h， 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：

  methyl α-L-sorbopyranoside 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 7.0h， 生成 (2S,3R,4R,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol
  参考文献：
  名称：

  Synthesis of 2,3,4,6-tetra-O-benzyl-l-idopyranose

  摘要：

  DOI：

  10.1016/s0008-6215(00)85231-3

文献信息

• Studies on the synthesis of valienamine and 1-epi-valienamine starting from d-glucose or l-sorbose
  作者：Ian Cumpstey、Sebastian Gehrke、Sayeh Erfan、Riccardo Cribiu

  DOI：10.1016/j.carres.2008.04.010

  日期：2008.7

  Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either D-glucose or L-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.

  从D-葡萄糖或L-山梨糖开始，并采用闭环复分解作为关键步骤，报道了两种合成途径形成瓦伦胺的碳环前体。据报道1-表戊烯胺的低产率合成。讨论了基于氮的早期引入而从第三种可能的方法流向缬草胺的结果。
• Tetrahedron Lett. 2011, 52, 3802-3804
  作者：

  DOI：——

  日期：——
• Synthesis of 2,3,4,6-tetra-O-benzyl-l-idopyranose
  作者：Robert Helleur、Vanga S. Rao、Arthur S. Perlin

  DOI：10.1016/s0008-6215(00)85231-3

  日期：1981.2
• 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.