3,5-O-isopropylidene-2-O-methyl-D-xylono-1,4-lactone | 1310357-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-O-isopropylidene-2-O-methyl-D-xylono-1,4-lactone
• 英文别名: (4aR,7R,7aS)-7-methoxy-2,2-dimethyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-one
• CAS: 1310357-27-7
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: GJEMJEUEIPCDHO-DSYKOEDSSA-N

物化性质

• 沸点：
  323.7±42.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-O-isopropylidene-2-O-methyl-D-xylono-1,4-lactone 在 2,6-二甲基吡啶 、 三甲基铝 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (R)-2-((4R,5S)-2,2-dimethyl-5-(triethylsilyloxy)-1,3-dioxan-4-yl)-2-methoxyacetaldehyde
  参考文献：
  名称：

  Synthesis of Key Fragments of Leiodelide A

  摘要：

  The synthesis of all key fragments of the marine macrolide lelodelide A is described. The polyoxygenated northern subunit is derived from D-xylose, while the southern subunit is rapidly assembled via an aldol reaction and Horner-Wadsworth-Emmons olefination. This highly convergent approach will allow for rapid modification and assembly of several isomers of lelodelide A, which may be necessary considering the assignment of leiodelide B has been previously shown to be incorrect.

  DOI：

  10.1021/ol201183f
• 作为产物：
  描述：

  D-吡喃木糖 在 溴 、 potassium carbonate 、 CSA 作用下， 以 水 、 丙酮 为溶剂， 反应 4.5h， 生成 3,5-O-isopropylidene-2-O-methyl-D-xylono-1,4-lactone
  参考文献：
  名称：

  Synthesis of Key Fragments of Leiodelide A

  摘要：

  The synthesis of all key fragments of the marine macrolide lelodelide A is described. The polyoxygenated northern subunit is derived from D-xylose, while the southern subunit is rapidly assembled via an aldol reaction and Horner-Wadsworth-Emmons olefination. This highly convergent approach will allow for rapid modification and assembly of several isomers of lelodelide A, which may be necessary considering the assignment of leiodelide B has been previously shown to be incorrect.

  DOI：

  10.1021/ol201183f

文献信息

• Synthesis of Key Fragments of Leiodelide A
  作者：Mathieu F. Chellat、Nicolas Proust、Matthew G. Lauer、James P. Stambuli

  DOI：10.1021/ol201183f

  日期：2011.6.17

  The synthesis of all key fragments of the marine macrolide lelodelide A is described. The polyoxygenated northern subunit is derived from D-xylose, while the southern subunit is rapidly assembled via an aldol reaction and Horner-Wadsworth-Emmons olefination. This highly convergent approach will allow for rapid modification and assembly of several isomers of lelodelide A, which may be necessary considering the assignment of leiodelide B has been previously shown to be incorrect.