dimethyl ((2,3:4,5-di-O-isopropylidene-D-arabinonyl)methyl)phosphonate | 55644-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl ((2,3:4,5-di-O-isopropylidene-D-arabinonyl)methyl)phosphonate
• 英文别名: 2-[dimethoxy(oxido)phosphaniumyl]-1-[(4S,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone
• CAS: 55644-26-3
• 化学式: C₁₄H₂₅O₈P
• 分子量: 352.321
• InChiKey: HWRBAERZMUJLEG-IJLUTSLNSA-N

物化性质

• 沸点：
  425.7±45.0 °C(predicted)
• 密度：
  1.201±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  95.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl ((2,3:4,5-di-O-isopropylidene-D-arabinonyl)methyl)phosphonate 在 氢气 作用下， 以99%的产率得到D-fructose 1-deoxy 1-phosphonic acid
  参考文献：
  名称：

  Chorghade, Mukund S.; Cseke, Csaba T., Heterocycles, 1995, vol. 40, # 1, p. 213 - 222

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氟-6-硝基苯胺 在 正丁基锂 、 溴 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.25h， 生成 dimethyl ((2,3:4,5-di-O-isopropylidene-D-arabinonyl)methyl)phosphonate
  参考文献：
  名称：

  Preparation of Sugar-Derived .beta.-Keto Phosphonates and Their Use in the Synthesis of Higher Sugars

  摘要：

  Sugar-derived beta-keto phosphonates 5, 6, 7, and 8 were synthesised by the acylation of lithium dimethyl methylphosphonate with the corresponding methyl glycuronates 1, 2, and 3 and glyconate 4 in THF at -78 degrees C, respectively. Wadsworth-Emmons reaction of 5, 6, 7, and 8 with various sugar-derived aldehydes proceeded in good yield to produce higher sugar enones. Similarly, C-2 symmetric bis phosphonate 28 derived from L-tartrate 27 was prepared and condensed with various sugar-derived aldehydes to provide C-2 symmetric bis enones in moderate yields. Treatment of the glucose-derived beta-keto phosphonate 5 with various aldehydes and excess Cs2CO3 resulted in complete cis elimination of the C-4 benzyl group along with the Wadsworth-Emmons reaction, leading to cross-conjugated dienones.

  DOI：

  10.1021/jo00100a047

文献信息

• Narkunan, K; Nagarajan, M, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 607 - 608
  作者：Narkunan, K、Nagarajan, M

  DOI：——

  日期：——
• Preparation of Sugar-Derived .beta.-Keto Phosphonates and Their Use in the Synthesis of Higher Sugars
  作者：K. Narkunan、M. Nagarajan

  DOI：10.1021/jo00100a047

  日期：1994.10

  Sugar-derived beta-keto phosphonates 5, 6, 7, and 8 were synthesised by the acylation of lithium dimethyl methylphosphonate with the corresponding methyl glycuronates 1, 2, and 3 and glyconate 4 in THF at -78 degrees C, respectively. Wadsworth-Emmons reaction of 5, 6, 7, and 8 with various sugar-derived aldehydes proceeded in good yield to produce higher sugar enones. Similarly, C-2 symmetric bis phosphonate 28 derived from L-tartrate 27 was prepared and condensed with various sugar-derived aldehydes to provide C-2 symmetric bis enones in moderate yields. Treatment of the glucose-derived beta-keto phosphonate 5 with various aldehydes and excess Cs2CO3 resulted in complete cis elimination of the C-4 benzyl group along with the Wadsworth-Emmons reaction, leading to cross-conjugated dienones.
• Chorghade, Mukund S.; Cseke, Csaba T., Heterocycles, 1995, vol. 40, # 1, p. 213 - 222
  作者：Chorghade, Mukund S.、Cseke, Csaba T.

  DOI：——

  日期：——