(R)-1-[(3R,4R)-4-((R)-1,2-Dihydroxy-ethyl)-1,3,4,6-tetrahydro-benzo[f][1,4]dioxocin-3-yl]-ethane-1,2-diol | 190731-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (R)-1-[(3R,4R)-4-((R)-1,2-Dihydroxy-ethyl)-1,3,4,6-tetrahydro-benzo[f][1,4]dioxocin-3-yl]-ethane-1,2-diol
• 英文别名: (1R)-1-[(3R,4R)-4-[(1R)-1,2-dihydroxyethyl]-1,3,4,6-tetrahydro-2,5-benzodioxocin-3-yl]ethane-1,2-diol
• CAS: 190731-37-4
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: NAXCMZZWCJIIAB-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (R)-1-[(3R,4R)-4-((R)-1,2-Dihydroxy-ethyl)-1,3,4,6-tetrahydro-benzo[f][1,4]dioxocin-3-yl]-ethane-1,2-diol 生成 (3R,4R)-3,4-Bis-(R)-oxiranyl-1,3,4,6-tetrahydro-benzo[f][1,4]dioxocine
  参考文献：
  名称：

  A Practical Approach to the Synthesis of Dianhydro Sugars

  摘要：

  Chiral tetrols derived from various carbohydrate precursors have been converted into the corresponding dianhydro sugar derivatives in a one pot procedure. The course of reaction very much depends upon the protecting groups used. In case of D-mannitol and sorbitol, it has been shown that when 3,4-hydroxy groups are protected as trans-acetonide group, the present methodology furnished exclusively 1,2 : 5,6-dianhydro derivatives in excellent yield. However, if the 3,4-hydroxy groups are protected with benzyl group a mixture of products consisting of dianhydro sugar, a furan and a bicyclo[2.2.2]octane derivatives were obtained. This method has also been used to synthesize dianhydro sugars in which the two diol moieties are placed adjacent to each other or separated by one or more carbon atoms.

  DOI：

  10.1080/00397919708004082
• 作为产物：
  描述：

  1,2:5,6-bis-O-(1-methylethylidene)-D-mannitol 在 sodium hydroxide 、 叔丁胺氢溴酸盐 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 (R)-1-[(3R,4R)-4-((R)-1,2-Dihydroxy-ethyl)-1,3,4,6-tetrahydro-benzo[f][1,4]dioxocin-3-yl]-ethane-1,2-diol
  参考文献：
  名称：

  A Practical Approach to the Synthesis of Dianhydro Sugars

  摘要：

  Chiral tetrols derived from various carbohydrate precursors have been converted into the corresponding dianhydro sugar derivatives in a one pot procedure. The course of reaction very much depends upon the protecting groups used. In case of D-mannitol and sorbitol, it has been shown that when 3,4-hydroxy groups are protected as trans-acetonide group, the present methodology furnished exclusively 1,2 : 5,6-dianhydro derivatives in excellent yield. However, if the 3,4-hydroxy groups are protected with benzyl group a mixture of products consisting of dianhydro sugar, a furan and a bicyclo[2.2.2]octane derivatives were obtained. This method has also been used to synthesize dianhydro sugars in which the two diol moieties are placed adjacent to each other or separated by one or more carbon atoms.

  DOI：

  10.1080/00397919708004082