(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 | 135604-82-9

• 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: (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
• CAS: 135604-82-9
• 化学式: C₃₇H₆₆O₄Si₂
• 分子量: 631.1
• InChiKey: UMCMKLJPFPGRHG-RXYRKFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.78
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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 disodium hydrogenphosphate 、 sodium amalgam 、 lithium aluminium tetrahydride 、 正丁基锂 、 1,10-菲罗啉 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 PRI-2168
  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)-5-Acetoxy-3-hydroperoxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentanoic acid methyl ester 在 咪唑 、 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.58h， 生成 (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
  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