1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol | 866413-94-7

• 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: 1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol
• 英文别名: (2R,3R,4R,5S,6S)-oct-7-ene-1,2,3,4,5,6-hexol
• CAS: 866413-94-7
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: JZGSGLXIHQVWFJ-BZCSJUTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol 在 臭氧 、 二甲基硫 作用下， 以 甲醇 为溶剂， 以91%的产率得到D-glycero-D-gulo-heptose
  参考文献：
  名称：

  Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters

  摘要：

  A procedure is described for acyloxyallylation of unprotected aldoses with two functionalized reagents: 3-bromopropenyl acetate and 3-bromopropenyl benzoate. The reaction is performed in ethanol or a dioxane/water mixture in the presence of indium metal. The products are deesterified in the workup to afford unsaturated polyols, which are isolated as mixtures of two diastereomers. The major diastereomers are subjected to ozonolysis to afford new aldoses, which have been elongated by two carbon atoms compared to the starting materials. The new aldoses all have lyxo configuration at positions 2, 3, and 4.

  DOI：

  10.1021/jo051297s
• 作为产物：
  描述：

  阿拉伯糖 在 indium 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol
  参考文献：
  名称：

  Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters

  摘要：

  A procedure is described for acyloxyallylation of unprotected aldoses with two functionalized reagents: 3-bromopropenyl acetate and 3-bromopropenyl benzoate. The reaction is performed in ethanol or a dioxane/water mixture in the presence of indium metal. The products are deesterified in the workup to afford unsaturated polyols, which are isolated as mixtures of two diastereomers. The major diastereomers are subjected to ozonolysis to afford new aldoses, which have been elongated by two carbon atoms compared to the starting materials. The new aldoses all have lyxo configuration at positions 2, 3, and 4.

  DOI：

  10.1021/jo051297s

文献信息

• Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters
  作者：Anders Palmelund、Robert Madsen

  DOI：10.1021/jo051297s

  日期：2005.9.1

  A procedure is described for acyloxyallylation of unprotected aldoses with two functionalized reagents: 3-bromopropenyl acetate and 3-bromopropenyl benzoate. The reaction is performed in ethanol or a dioxane/water mixture in the presence of indium metal. The products are deesterified in the workup to afford unsaturated polyols, which are isolated as mixtures of two diastereomers. The major diastereomers are subjected to ozonolysis to afford new aldoses, which have been elongated by two carbon atoms compared to the starting materials. The new aldoses all have lyxo configuration at positions 2, 3, and 4.