(5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-al | 135604-76-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-al
• 英文别名: (5Z,7E)-(1S,3R)-1,3-bis[[(1,1-dimethylethyl)dimethyl-silyl]oxy]-9,10-secochola-5,7,10(19)-trien-24-al；(4R)-4-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]pentanal
• CAS: 135604-76-1
• 化学式: C₃₆H₆₄O₃Si₂
• 分子量: 601.073
• InChiKey: IGQUBKWSJZOICR-KVELHUOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

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-al 在 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 1,10-菲罗啉 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 (24b R)-24,24-dihomo-1,25-dihydroxyergocalciferol
  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：

  methyl (5Z,7E)-(1S,3R)-1,3-dihydroxy-9,10-secochola-5,7,10-⁽¹⁹⁾-trien-24-oate 在 咪唑 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-al
  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

• Vitamin D derivatives with cyclic substructures in the side chains, process and intermediate products for their production, and the use for the production of pharmaceutical agents
  申请人：Schering Aktiengesellschaft

  公开号：US06603031B1

  公开（公告）日：2003-08-05

  The invention relates to vitamin D derivatives of general formula I, process for their production, intermediate products of the process as well as the use for the production of pharmaceutical agents.

  这项发明涉及一般式I的维生素D衍生物，其生产方法，生产过程的中间产物以及用于生产药物制剂的用途。