4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene | 827032-51-9

• 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: 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene
• CAS: 827032-51-9
• 化学式: C₅₇H₁₁₆O₅Si₅
• 分子量: 1021.97
• InChiKey: CSTLWEMTUYGUIQ-PZRRXXIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.87
• 重原子数：
  67.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以38.4 mg的产率得到(20R)-24-Hydroxy-19-norgeminivitamin D3
  参考文献：
  名称：

  Calcitriol Derivatives with Two Different Side Chains at C-20. II. Diastereoselective Syntheses of the Metabolically Produced 24(R)-Hydroxygemini

  摘要：

  Vitamin D derivatives containing two side chains emanating at C-20 are known as gemini. We have recently synthesized two gemini which are related to calcitriol and 19-norcalcitriol containing two identical side chains. The metabolism of these species involves 24(R)hydroxylation on one of the side chains. To determine the outcome of this diastereospecific transformation, we synthesized both C-20 epimeric pairs containing the 24(R)-hydroxy group in the gemini and 19-norgemini series. On the basis of the availability of these reference compounds, it was shown that the metabolic hydroxylation occurred at the pro-R side chain in both gemini compounds. In comparison to the parent compounds, the 24-hydroxygemini required higher doses to increase blood calcium levels in mice and to suppress INF-gamma release in MLR.

  DOI：

  10.1021/jm049340b
• 作为产物：
  描述：

  (1R,3aR,4S,7aR)-1-{(R)-5-hydroxy-5-methyl-1-[2-((R)-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl)ethyl]hexyl}-7a-methyloctahydroinden-4-ol 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 正丁基锂 、 Celite 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 130.67h， 生成 4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-1-[4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-indene
  参考文献：
  名称：

  Calcitriol Derivatives with Two Different Side Chains at C-20. II. Diastereoselective Syntheses of the Metabolically Produced 24(R)-Hydroxygemini

  摘要：

  Vitamin D derivatives containing two side chains emanating at C-20 are known as gemini. We have recently synthesized two gemini which are related to calcitriol and 19-norcalcitriol containing two identical side chains. The metabolism of these species involves 24(R)hydroxylation on one of the side chains. To determine the outcome of this diastereospecific transformation, we synthesized both C-20 epimeric pairs containing the 24(R)-hydroxy group in the gemini and 19-norgemini series. On the basis of the availability of these reference compounds, it was shown that the metabolic hydroxylation occurred at the pro-R side chain in both gemini compounds. In comparison to the parent compounds, the 24-hydroxygemini required higher doses to increase blood calcium levels in mice and to suppress INF-gamma release in MLR.

  DOI：

  10.1021/jm049340b