1,2:3,4-di-O-isopropylidene-β-L-xylo-3-hexulofuranose | 28412-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:3,4-di-O-isopropylidene-β-L-xylo-3-hexulofuranose
• 英文别名: 1,2:3,4-Di-O-isopropyliden-β-L-xylo-3-hexulose；(3aR,6S,6aR)-3a-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 28412-65-9
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: OWQKKJHZJSNKGW-FNOROQBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-xylo-3-hexulose 、 丙酮 在 硫酸 作用下， 反应 1.5h， 以75%的产率得到1,2:3,4-di-O-isopropylidene-β-L-xylo-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

文献信息

• Morgenlie, Svein, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 10, p. 745 - 748
  作者：Morgenlie, Svein

  DOI：——

  日期：——
• 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.