(1R,3aS,7aR)-4(E)-{2-[(R)-3-((R)-(tert-butyldimethylsilyloxy))-5-(tert-butyldimethylsilyloxy)cyclohexylidene]ethylidene}-7a-methyl-1-[(1S,4R)-5-methyl-1-(4-methyl-4-(triethylsilanyloxy)pentyl)-4,5-bis(triethylsilanyloxy)hexyl]octahydroindene | 770714-54-0

• 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: (1R,3aS,7aR)-4(E)-{2-[(R)-3-((R)-(tert-butyldimethylsilyloxy))-5-(tert-butyldimethylsilyloxy)cyclohexylidene]ethylidene}-7a-methyl-1-[(1S,4R)-5-methyl-1-(4-methyl-4-(triethylsilanyloxy)pentyl)-4,5-bis(triethylsilanyloxy)hexyl]octahydroindene
• 英文别名: [1R,3aR,7aR,4E]-4-{2(Z)-[3(S),5(R)-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-1-[5-methyl-1(S)-(4-methyl-4-triethylsilanyloxy-pentyl)-4(R),5-bis-triethylsilanyloxy-hexyl]-octahydro-indene；[1R,3aR,7aR,4E]-4-[2(Z)-[3(S),5(R)-bis(tert-butyldimethylsilanyloxy)-2-methylene-cyclohexylidene]-ethylidene]-7a-methyl-1-[5-methyl-1(S)-(4-methyl-4-triethylsilanyloxy-pentyl)-4(R),5-bis(triethylsilanyloxy)-hexyl]-octahydro-indene；[1R,3aR,7aR,4E]-4-{2(Z)-[3(S),5(R)-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethylidene}-7a-methyl-1-[5-methyl-1(S)-(4-methyl-4-triethylsilanyloxypentyl)-4(R),5-bis-triethylsilanyloxyhexyl]octahydroindene
• CAS: 770714-54-0
• 化学式: C₆₂H₁₂₄O₅Si₅
• 分子量: 1090.09
• InChiKey: IWKQAFXRESQGQF-LICGXZOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.74
• 重原子数：
  72.0
• 可旋转键数：
  29.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (1R,3aS,7aR)-4(E)-{2-[(R)-3-((R)-(tert-butyldimethylsilyloxy))-5-(tert-butyldimethylsilyloxy)cyclohexylidene]ethylidene}-7a-methyl-1-[(1S,4R)-5-methyl-1-(4-methyl-4-(triethylsilanyloxy)pentyl)-4,5-bis(triethylsilanyloxy)hexyl]octahydroindene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以93%的产率得到1,25-dihydroxy-21-(2R,3-dihydroxy-3-methyl-butyl)-20S-cholecalciferol
  参考文献：
  名称：

  GEMINI VITAMIN D3 COMPOUNDS AND METHODS OF USE THEREOF

  摘要：

  这项发明提供了双子座维生素D3化合物，使用这些化合物治疗与维生素D3相关疾病的方法以及含有这些化合物的药物组合物。

  公开号：

  US20080280859A1
• 作为产物：
  描述：

  (R)-6-[(1R,3aR,4S,7aR)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-2-methyl-7-phenylsulfanyl-heptan-2-ol 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 sodium-mercury amalgam (5%) 、 正丁基锂 、 六氟合硅酸 、 pyridinium dichromate 、 4-甲基苯磺酸吡啶 、 草酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 环己烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 78.26h， 生成 (1R,3aS,7aR)-4(E)-{2-[(R)-3-((R)-(tert-butyldimethylsilyloxy))-5-(tert-butyldimethylsilyloxy)cyclohexylidene]ethylidene}-7a-methyl-1-[(1S,4R)-5-methyl-1-(4-methyl-4-(triethylsilanyloxy)pentyl)-4,5-bis(triethylsilanyloxy)hexyl]octahydroindene
  参考文献：
  名称：

  WO2006/100285

  摘要：

  公开号：

文献信息

• WO2006/51106
  申请人：——

  公开号：——

  公开（公告）日：——
• Calcitriol Derivatives with Two Different Side Chains at C-20. II. Diastereoselective Syntheses of the Metabolically Produced 24(<i>R</i>)-Hydroxygemini
  作者：Hubert Maehr、Milan R. Uskokovic、Luciano Adorini、G. Satyanarayana Reddy

  DOI：10.1021/jm049340b

  日期：2004.12.1

  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.