2-[(4R,6R)-6-[[(4S,6S)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetonitrile | 620605-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(4R,6R)-6-[[(4S,6S)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetonitrile
• CAS: 620605-72-3
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: NYWQQIMMQZMUTE-NMWPEEMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(4R,6R)-6-[[(4S,6S)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetonitrile 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以70%的产率得到{(4S,6S)-6-[(4R,6R)-2,2-Dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetaldehyde
  参考文献：
  名称：

  Palladium(0)-Mediated Desymmetrization of Meso Tetraols:  An Approach to the C3−C17 Bis-oxane Segment of Phorboxazoles A and B

  摘要：

  [GRAPHICS]meso-Tetraol bis(allylic acetates) 2 and 5 were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled desymmetrization provided the desired bis-oxanes in greater than 98% ee. Bis-oxanes 1 and 4 represent potential synthetic intermediates for the C3-C17 subunits of phorboxazoles A and B.

  DOI：

  10.1021/ol0354775
• 作为产物：
  描述：

  [(4S,6S)-6-[[(4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]methanol 在 2,6-二甲基吡啶 、 18-冠醚-6 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.67h， 生成 2-[(4R,6R)-6-[[(4S,6S)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetonitrile
  参考文献：
  名称：

  Palladium(0)-Mediated Desymmetrization of Meso Tetraols:  An Approach to the C3−C17 Bis-oxane Segment of Phorboxazoles A and B

  摘要：

  [GRAPHICS]meso-Tetraol bis(allylic acetates) 2 and 5 were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled desymmetrization provided the desired bis-oxanes in greater than 98% ee. Bis-oxanes 1 and 4 represent potential synthetic intermediates for the C3-C17 subunits of phorboxazoles A and B.

  DOI：

  10.1021/ol0354775

文献信息

• Palladium(0)-Mediated Desymmetrization of Meso Tetraols:  An Approach to the C3−C17 Bis-oxane Segment of Phorboxazoles A and B
  作者：Brian S. Lucas、Steven D. Burke

  DOI：10.1021/ol0354775

  日期：2003.10.1

  [GRAPHICS]meso-Tetraol bis(allylic acetates) 2 and 5 were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled desymmetrization provided the desired bis-oxanes in greater than 98% ee. Bis-oxanes 1 and 4 represent potential synthetic intermediates for the C3-C17 subunits of phorboxazoles A and B.