(S)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-6-((1R,2S)-2-hydroxy-1-methyl-butyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde | 193416-26-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-6-((1R,2S)-2-hydroxy-1-methyl-butyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde
• CAS: 193416-26-1
• 化学式: C₂₀H₄₀O₄Si
• 分子量: 372.621
• InChiKey: OGZBYQPZEAZCOU-IYYNEKPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-6-((1R,2S)-2-hydroxy-1-methyl-butyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以64%的产率得到(S)-2-[(4R,5S,6S)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-oxo-butyl)-[1,3,2]dioxasilinan-4-yl]-propionaldehyde
  参考文献：
  名称：

  Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

  摘要：

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00617-0
• 作为产物：
  描述：

  (S)-2-[(4R,5S,6S)-2,2-Di-tert-butyl-6-((S)-1-[1,3]dithiolan-2-yl-ethyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one 在 mercury(II) perchlorate 、 phosphate buffer pH 7.4 、 三乙基硼氢化锂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (S)-2-[(4R,5R,6R)-2,2-Di-tert-butyl-6-((1R,2S)-2-hydroxy-1-methyl-butyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde
  参考文献：
  名称：

  Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

  摘要：

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00617-0