(5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-ol | 135604-75-0

• 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: (5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-ol
• CAS: 135604-75-0
• 化学式: C₃₆H₆₆O₃Si₂
• 分子量: 603.089
• InChiKey: CVWXWTXJDDZDJR-KVELHUOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.59
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-ol 在 正丁基锂 、 1,10-菲罗啉 、 草酰氯 、 二甲基亚砜 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of side-chain homologated analogs of 1,25-dihydroxycholecalciferol and 1,25-dihydroxyergocalciferol

  摘要：

  A novel synthesis of side-chain homologated analogs of vitamin D isomers has been described. The synthesis allows for the insertion of the double bond into the C-24 position of the side chain. The key synthetic step involves the coupling of a new C24-vitamin D synthon with the respective side-chain fragment. The method is illustrated by the preparation of (24E)-24,24a-dehydro-24,24-dihomo-1,25-dihydroxycholecalciferol (1) and (24b R)- and (24b S)-24,24-dihomo-1,25-dihydroxyergocalciferols (2 and 3). Trans geometry of the newly formed double bond in the side chain was confirmed by high field nuclear magnetic resonance spectra.

  DOI：

  10.1016/0039-128x(91)90052-w
• 作为产物：
  描述：

  (R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentanoic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以67%的产率得到(5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-ol
  参考文献：
  名称：

  Synthesis of side-chain homologated analogs of 1,25-dihydroxycholecalciferol and 1,25-dihydroxyergocalciferol

  摘要：

  A novel synthesis of side-chain homologated analogs of vitamin D isomers has been described. The synthesis allows for the insertion of the double bond into the C-24 position of the side chain. The key synthetic step involves the coupling of a new C24-vitamin D synthon with the respective side-chain fragment. The method is illustrated by the preparation of (24E)-24,24a-dehydro-24,24-dihomo-1,25-dihydroxycholecalciferol (1) and (24b R)- and (24b S)-24,24-dihomo-1,25-dihydroxyergocalciferols (2 and 3). Trans geometry of the newly formed double bond in the side chain was confirmed by high field nuclear magnetic resonance spectra.

  DOI：

  10.1016/0039-128x(91)90052-w

文献信息

• Kutner, A., Polish Journal of Chemistry, 1993, vol. 67, # 4, p. 759 - 761
  作者：Kutner, A.

  DOI：——

  日期：——