(4R)-2-[(1S)-1-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]ethyl]-4,5-dihydroxy-5-methylhexanenitrile | 937182-43-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-2-[(1S)-1-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]ethyl]-4,5-dihydroxy-5-methylhexanenitrile
• CAS: 937182-43-9
• 化学式: C₁₉H₃₃NO₃
• 分子量: 323.476
• InChiKey: SQHSMROYHZJSOV-SOHUWGBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  84.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-2-[(1S)-1-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]ethyl]-4,5-dihydroxy-5-methylhexanenitrile 在 六甲基磷酰三胺 、 氢化钾 作用下， 以 乙醚 、 叔丁醇 为溶剂， 以39%的产率得到(1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol
  参考文献：
  名称：

  d- and l-Serine, useful synthons for the synthesis of 24-hydroxyvitamin D3 metabolites. A formal synthesis of 1α,24R,25-(OH)3-D3, 24R,25-(OH)2-D3 and 24S,25-(OH)2-D3

  摘要：

  D- and L-Serine have been used for the enantioselective synthesis of tosylates 7a and 7b, useful building blocks for the synthesis of triols 5a and 5b which have already been obtained via a diastereoselective synthesis and used for the synthesis of 2a, 2b and 2c. We have thus performed a formal synthesis of 24S,25-(OH)(2)-D-3, 24R,25-(OH)(2)-D-3 and 1 alpha,24R,25-(OH)(3)-D-3. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.027
• 作为产物：
  描述：

  (R)-(+)-3-methyl-1,2,3-butanetriol 在 吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (4R)-2-[(1S)-1-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]ethyl]-4,5-dihydroxy-5-methylhexanenitrile
  参考文献：
  名称：

  d- and l-Serine, useful synthons for the synthesis of 24-hydroxyvitamin D3 metabolites. A formal synthesis of 1α,24R,25-(OH)3-D3, 24R,25-(OH)2-D3 and 24S,25-(OH)2-D3

  摘要：

  D- and L-Serine have been used for the enantioselective synthesis of tosylates 7a and 7b, useful building blocks for the synthesis of triols 5a and 5b which have already been obtained via a diastereoselective synthesis and used for the synthesis of 2a, 2b and 2c. We have thus performed a formal synthesis of 24S,25-(OH)(2)-D-3, 24R,25-(OH)(2)-D-3 and 1 alpha,24R,25-(OH)(3)-D-3. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.027