D-arabino-3-hexulose | 150950-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-arabino-3-hexulose
• 英文别名: (2S,3R,4R)-2-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-triol
• CAS: 150950-15-5
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: JKIAQWMSGAOABR-KAZBKCHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-arabino-3-hexulose 、 丙酮 在 硫酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 1,2:3,4-di-O-isopropylidene-β-D-arabino-3-hexulofuranose 、 1,2:3,4-di-O-isopropylidene-α-D-arabino-3-hexulofuranose 、 1,2:4,5-di-O-isopropylidene-D-arabino-3-hexulofuranose
  参考文献：
  名称：

  Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols

  摘要：

  A simple, but low-yielding method for the synthesis of 3-hexuloses has been elaborated. Oxidation of 1,2:5,6-di-O-isopropylidenehexitols with bromine in the presence of barium carbonate, followed by mild-acid hydrolysis of the oxidation products gave the free hexuloses. Oxidation occurred at only one of the carbon atoms bearing free hydroxyl groups. From the D-mannitol derivative, D-arabino-3-hexulose was obtained via the di-O-isopropylidene derivative, whereas the D-glucitol derivative gave a mixture of the 1,2:5,6-di-O-isoprpylidene derivatives of L-xylo- and D-ribo-3-hexulose, separable by column chromatography. Mild-acid hydrolysis of the oxidation products afforded the free hexuloses. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00217-8
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-D-arabino-3-hexulose 在 硫酸 作用下， 反应 3.0h， 以88%的产率得到D-arabino-3-hexulose
  参考文献：
  名称：

  Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols

  摘要：

  A simple, but low-yielding method for the synthesis of 3-hexuloses has been elaborated. Oxidation of 1,2:5,6-di-O-isopropylidenehexitols with bromine in the presence of barium carbonate, followed by mild-acid hydrolysis of the oxidation products gave the free hexuloses. Oxidation occurred at only one of the carbon atoms bearing free hydroxyl groups. From the D-mannitol derivative, D-arabino-3-hexulose was obtained via the di-O-isopropylidene derivative, whereas the D-glucitol derivative gave a mixture of the 1,2:5,6-di-O-isoprpylidene derivatives of L-xylo- and D-ribo-3-hexulose, separable by column chromatography. Mild-acid hydrolysis of the oxidation products afforded the free hexuloses. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00217-8

文献信息

• Formation of 3-hexuloses in aldol reactions, analysis of the products as their O-isopropylidene derivatives by GC–MS
  作者：Dag Ekeberg、Svein Morgenlie

  DOI：10.1016/j.carres.2004.06.018

  日期：2004.9

  for analysis of mixtures of 3-hexuloses by gas chromatography mass spectrometry of their di-O-isopropylidene derivatives has been elaborated. The origin of characteristic fragment ions in the mass spectra is suggested on the basis of the spectra of d(12) analogues, obtained by acetonation with acetone-d(6) and on MS/MS investigations. The method has been applied to product mixtures from aldol reactions

  已经阐述了通过气相色谱质谱法分析3-己糖的二-O-异亚丙基衍生物来分析3-己糖的混合物的方法。根据d（12）类似物的光谱（通过用丙酮-d（6）进行丙酮化获得）和MS / MS研究，提出了质谱中特征性碎片离子的起源。该方法已应用于甘油-十六烷基糖和乙醇醛之间，2-戊糖和甲醛之间的醛醇缩合反应的产物混合物。一个有趣的结果是在赤藓-2-戊糖和甲醛之间的碱催化反应中形成了具有高度立体选择性的核糖-3-己糖。
• Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols
  作者：Dag Ekeberg、Svein Morgenlie、Yngve Stenstrøm

  DOI：10.1016/s0008-6215(01)00217-8

  日期：2001.9

  A simple, but low-yielding method for the synthesis of 3-hexuloses has been elaborated. Oxidation of 1,2:5,6-di-O-isopropylidenehexitols with bromine in the presence of barium carbonate, followed by mild-acid hydrolysis of the oxidation products gave the free hexuloses. Oxidation occurred at only one of the carbon atoms bearing free hydroxyl groups. From the D-mannitol derivative, D-arabino-3-hexulose was obtained via the di-O-isopropylidene derivative, whereas the D-glucitol derivative gave a mixture of the 1,2:5,6-di-O-isoprpylidene derivatives of L-xylo- and D-ribo-3-hexulose, separable by column chromatography. Mild-acid hydrolysis of the oxidation products afforded the free hexuloses. (C) 2001 Elsevier Science Ltd. All rights reserved.