(R)-2-((4R,5S)-2,2-dimethyl-5-(triethylsilyloxy)-1,3-dioxan-4-yl)-2-methoxyacetaldehyde | 1310357-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-((4R,5S)-2,2-dimethyl-5-(triethylsilyloxy)-1,3-dioxan-4-yl)-2-methoxyacetaldehyde
• CAS: 1310357-41-5
• 化学式: C₁₅H₃₀O₅Si
• 分子量: 318.486
• InChiKey: YMWQDAVVQBAPLP-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-2-((4R,5S)-2,2-dimethyl-5-(triethylsilyloxy)-1,3-dioxan-4-yl)-2-methoxyacetaldehyde 、 (4-(benzyloxy)butan-2-yl)triphenylphosphonium bromide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (((4R,5R)-4-((S,Z)-5-(benzyloxy)-1-methoxy-3-methylpent-2-en-1-yl)-2,2-dimethyl-1,3-dioxan-5-yl)oxy)triethylsilane 、 (((4R,5R)-4-((S,E)-5-(benzyloxy)-1-methoxy-3-methylpent-2-en-1-yl)-2,2-dimethyl-1,3-dioxan-5-yl)oxy)triethylsilane
  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：

  (R)-2-((4S,5S)-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl)-N,2-dimethoxy-N-methylacetamide 在 2,6-二甲基吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 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