(2S)-3-[4-[(2S)-2,3-dihydroxypropoxy]phenoxy]propane-1,2-diol | 178237-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S)-3-[4-[(2S)-2,3-dihydroxypropoxy]phenoxy]propane-1,2-diol
• CAS: 178237-88-2
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: PUCRCVZEFZKZAL-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-3-[4-[(2S)-2,3-dihydroxypropoxy]phenoxy]propane-1,2-diol 在 氢溴酸 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 48.5h， 生成 1,4-bis-(2-(S)-oxiranylmethoxy)benzene
  参考文献：
  名称：

  Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

  摘要：

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.

  DOI：

  10.1021/jo971324h
• 作为产物：
  描述：

  1,4-二(丙-2-烯氧基)苯 在 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 15.0h， 以80%的产率得到(2S)-3-[4-[(2S)-2,3-dihydroxypropoxy]phenoxy]propane-1,2-diol
  参考文献：
  名称：

  Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

  摘要：

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.

  DOI：

  10.1021/jo971324h

文献信息

• A practical route to enantiopure 1,2-aminoalcohols
  作者：Han-Ting Chang、K.Barry Sharpless

  DOI：10.1016/0040-4039(96)00534-5

  日期：1996.5

  A series of enantiopure aminoalcohols were synthesized from the corresponding diols by activation of the diols as cyclic carbonates, azide opening of the carbonates, and hydrogenation of the resulting azidoalcohols. Factors affecting the azide opening of the carbonates, a simple workup procedure, and a large scale synthesis of (1R,2S)-(−)-2-amino-1,2-diphenylethanol are described.

  通过活化作为环状碳酸酯的二醇，将碳酸酯的叠氮化物打开以及将所得的叠氮醇氢化来从相应的二醇合成一系列对映体纯的氨基醇。描述了影响碳酸盐的叠氮化物开口的因素，简单的后处理程序以及大规模合成（1R，2S）-（-）-2-氨基-1,2-二苯基乙醇的方法。
• A General, Practical, and Versatile Strategy for Accessing ω-Functional 1,2-Diols of High Enantiomeric Excess
  作者：Thomas R. Hoye、Michael J. Mayer、Tricia J. Vos、Zhixiong Ye

  DOI：10.1021/jo980844p

  日期：1998.11.1