2,5-anhydro-D-glucose | 18439-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-D-glucose
• 英文别名: (2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbaldehyde
• CAS: 18439-33-3
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: LKAPTZKZHMOIRE-SLPGGIOYSA-N

物化性质

• 沸点：
  404.7±45.0 °C(Predicted)
• 密度：
  1.639±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-D-glucose 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 24.0h， 以91%的产率得到2,5-脱水-D-葡萄糖醇
  参考文献：
  名称：

  Sequential Removal of Monosaccharides from the Reducing End of Oligosaccharides. 2. Fundamental Studies of a Reaction between Hydrazino Compounds and Sugars Having a Glycosyl Moiety on a Carbon Atom Adjacent to a Carbonyl Group

  摘要：

  Hydrazine and certain hydrazino derivatives react with sugars having a glycosidic substituent, where the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto group of the aglycon, resulting in cleavage of the glycosidic linkage. The reaction proceeds whether the glycon is of the alpha or beta configuration. The released glycosyl moiety, in the presence of excess hydrazino compound, reacts further to give a hydrazone derivative. Removal of the hydrazone group gives the reducing sugar derived from the glycon.

  DOI：

  10.1021/jo00130a026
• 作为产物：
  描述：

  2,5-anhydro-D-glucose pentafluorophenylhydrazone 在 苯甲醛 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以86%的产率得到2,5-anhydro-D-glucose
  参考文献：
  名称：

  Sequential Removal of Monosaccharides from the Reducing End of Oligosaccharides. 2. Fundamental Studies of a Reaction between Hydrazino Compounds and Sugars Having a Glycosyl Moiety on a Carbon Atom Adjacent to a Carbonyl Group

  摘要：

  Hydrazine and certain hydrazino derivatives react with sugars having a glycosidic substituent, where the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto group of the aglycon, resulting in cleavage of the glycosidic linkage. The reaction proceeds whether the glycon is of the alpha or beta configuration. The released glycosyl moiety, in the presence of excess hydrazino compound, reacts further to give a hydrazone derivative. Removal of the hydrazone group gives the reducing sugar derived from the glycon.

  DOI：

  10.1021/jo00130a026

文献信息

• Levene, Journal of Biological Chemistry, 1919, vol. 39, p. 73
  作者：Levene

  DOI：——

  日期：——
• Re-examination of the acid hydrolysis of 5,6-anhydro-1,2-O-isopropylidene-β-l-idofuranose
  作者：Neil Baggett、Amarjit K. Samra

  DOI：10.1016/0008-6215(84)85115-0

  日期：1984.4