(1R)-1-((5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (1R)-1-((5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol
• 英文别名: (1R)-1-[(5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]ethane-1,2-diol
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: IENSYSQTQGXKIV-QYNFOATHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-((5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol 在 sodium periodate 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 (5R)-5-hydroxy-2-phenyl-1,3-dioxane-4-carbaldehyde
  参考文献：
  名称：

  Formal synthesis of 4-diphosphocytidyl-2-C-methyl d-erythritol from d-(+)-arabitol

  摘要：

  2-C-Methyl-D-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), another key intermediate of the non-mevalonate pathway. As this pathway is non-existent in higher animals, including humans, it represents great opportunities for novel antimicrobial development. To facilitate the in-depth studies of this pathway, we reported here a formal synthesis of CDP-ME through a new synthesis of 2-C-methyl-D-erythritol-4-phosphoric acid from D-(+)-arabitol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.020
• 作为产物：
  描述：

  D-Arabitol 、 苯甲醛 在 盐酸 作用下， 以 水 为溶剂， 反应 72.0h， 以73%的产率得到(1R)-1-((5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol
  参考文献：
  名称：

  Formal synthesis of 4-diphosphocytidyl-2-C-methyl d-erythritol from d-(+)-arabitol

  摘要：

  2-C-Methyl-D-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), another key intermediate of the non-mevalonate pathway. As this pathway is non-existent in higher animals, including humans, it represents great opportunities for novel antimicrobial development. To facilitate the in-depth studies of this pathway, we reported here a formal synthesis of CDP-ME through a new synthesis of 2-C-methyl-D-erythritol-4-phosphoric acid from D-(+)-arabitol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.020

文献信息

• Formal synthesis of 4-diphosphocytidyl-2-C-methyl d-erythritol from d-(+)-arabitol
  作者：Sina I. Odejinmi、Rafael G. Rascon、Wyman Chen、Kent Lai

  DOI：10.1016/j.tet.2012.08.020

  日期：2012.10

  2-C-Methyl-D-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), another key intermediate of the non-mevalonate pathway. As this pathway is non-existent in higher animals, including humans, it represents great opportunities for novel antimicrobial development. To facilitate the in-depth studies of this pathway, we reported here a formal synthesis of CDP-ME through a new synthesis of 2-C-methyl-D-erythritol-4-phosphoric acid from D-(+)-arabitol. (C) 2012 Elsevier Ltd. All rights reserved.