(1S,2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-pyridin-2-yl-propan-1-ol | 684214-40-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1S,2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-pyridin-2-yl-propan-1-ol
• 英文别名: (1S,2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-pyridin-2-ylpropan-1-ol
• CAS: 684214-40-2
• 化学式: C₃₂H₄₇NO₃
• 分子量: 493.73
• InChiKey: CFKCJWUBFCZJIG-UXVZYSSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  51.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-pyridin-2-yl-propan-1-ol 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 反应 24.0h， 以71%的产率得到(3S,8R,9S,10S,13S,14S,17R)-17-((1S,2S)-2-Hydroxy-1-methyl-2-piperidin-2-yl-ethyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  Stereoselective Addition of Pyridyl Lithium to 22‐Aldehyde Steroid. Synthesis of 22‐Piperidin‐yl‐pregnan‐3β, 22(S)‐diol

  摘要：

  A short synthesis of two new 22-piperidin-yl-pregnan-5-en-3beta,8,22S-ols from 23,24-bisnor-5-cholenic acid-3beta-ol is described. The addition of pyridyl lithium to 3beta-tetrahydropyranyloxy-23-bisnorchol-5-en-22-al 5 affords the 22alpha, 22S hydroxy configuration with high diastereoselectivity as measured by NMR (84-90% de).

  DOI：

  10.1081/scc-120027294
• 作为产物：
  描述：

  20S-hydroxymethyl-3β-(tetrahydropyran-2'-yl)oxypregn-5-ene 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (1S,2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-pyridin-2-yl-propan-1-ol
  参考文献：
  名称：

  Stereoselective Addition of Pyridyl Lithium to 22‐Aldehyde Steroid. Synthesis of 22‐Piperidin‐yl‐pregnan‐3β, 22(S)‐diol

  摘要：

  A short synthesis of two new 22-piperidin-yl-pregnan-5-en-3beta,8,22S-ols from 23,24-bisnor-5-cholenic acid-3beta-ol is described. The addition of pyridyl lithium to 3beta-tetrahydropyranyloxy-23-bisnorchol-5-en-22-al 5 affords the 22alpha, 22S hydroxy configuration with high diastereoselectivity as measured by NMR (84-90% de).

  DOI：

  10.1081/scc-120027294

文献信息

• Stereoselective Addition of Pyridyl Lithium to 22‐Aldehyde Steroid. Synthesis of 22‐Piperidin‐yl‐pregnan‐3β, 22(S)‐diol
  作者：Gonzalo Visbal、Alvaro Alvarez‐Aular

  DOI：10.1081/scc-120027294

  日期：2004.12.31

  A short synthesis of two new 22-piperidin-yl-pregnan-5-en-3beta,8,22S-ols from 23,24-bisnor-5-cholenic acid-3beta-ol is described. The addition of pyridyl lithium to 3beta-tetrahydropyranyloxy-23-bisnorchol-5-en-22-al 5 affords the 22alpha, 22S hydroxy configuration with high diastereoselectivity as measured by NMR (84-90% de).