(2R,3S)-2-((4R,5S,6S)-2,2-di-tert-butyl-6-((R)-1-hydroxypropan-2-yl)-5-methyl-1,3,2-dioxasilinan-4-yl)pentan-3-ol | 193416-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,3S)-2-((4R,5S,6S)-2,2-di-tert-butyl-6-((R)-1-hydroxypropan-2-yl)-5-methyl-1,3,2-dioxasilinan-4-yl)pentan-3-ol
• 英文别名: (2R,3S)-2-[(4R,5S,6S)-2,2-Di-tert-butyl-6-((R)-2-hydroxy-1-methyl-ethyl)-5-methyl-[1,3,2]dioxasilinan-4-yl]-pentan-3-ol
• CAS: 193416-25-0
• 化学式: C₂₀H₄₂O₄Si
• 分子量: 374.637
• InChiKey: NSBYHNMUCYCWBT-IYYNEKPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 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：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-((4R,5S,6S)-2,2-di-tert-butyl-6-((R)-1-hydroxypropan-2-yl)-5-methyl-1,3,2-dioxasilinan-4-yl)pentan-3-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%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 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.25h， 生成 (2R,3S)-2-((4R,5S,6S)-2,2-di-tert-butyl-6-((R)-1-hydroxypropan-2-yl)-5-methyl-1,3,2-dioxasilinan-4-yl)pentan-3-ol
  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