(1R,3aR,7aR)-1-[(1R,4R)-4-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1-(4-methyl-4-(trimethylsilanyloxy)pentyl)-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-one | 792959-65-0

• 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,3aR,7aR)-1-[(1R,4R)-4-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1-(4-methyl-4-(trimethylsilanyloxy)pentyl)-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-one
• 英文别名: [1R,3aR,7aR]-1-[4(R)-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1(R)-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydro-inden-4-one；[1R,3aR,7aR]-1-[4(R)-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methyl-1(R)-(4-methyl-4-trimethylsilanyloxy-pentyl)-5-trimethylsilanyloxy-hexyl]-7a-methyl-octahydroinden-4-one；[1R,3aR,7aR]-1-[4(R)-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1(R)-(4-methyl-4-trimethylsilanyloxypentyl)trimethylsilanyloxyhexyl]-7a-methyloctahydroinden-4-one；(1R,3aR,7aR)-1-[(3R,6R)-3-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-2,10-dimethyl-2,10-bis(trimethylsilyloxy)undecan-6-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 792959-65-0
• 化学式: C₃₇H₇₆O₄Si₃
• 分子量: 669.265
• InChiKey: YZZCVWXZDWRMJE-PQBORFAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.63
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,3aR,7aR)-1-[(1R,4R)-4-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1-(4-methyl-4-(trimethylsilanyloxy)pentyl)-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-one 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.17h， 生成 1,25-dihydroxy-21-(2R,3-dihydroxy-3-methyl-butyl)-20R-cholecalciferol
  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：

  (2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate 在 吡啶 、 咪唑 、 甲醇 、 sodium amalgam 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 正丁基锂 、 Celite 、 fluorosilic acid 、 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 161.92h， 生成 (1R,3aR,7aR)-1-[(1R,4R)-4-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-5-methyl-1-(4-methyl-4-(trimethylsilanyloxy)pentyl)-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-one
  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

文献信息

• GEMINI VITAMIN D3 COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Adorini Luciano

  公开号：US20080280859A1

  公开（公告）日：2008-11-13

  The invention provides Gemini vitamin D 3 compounds, methods for using the compounds to treat vitamin D3 associated states and pharmaceutical compositions containing the compounds.

  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。
• [EN] USE OF VITAMIN D COMPOUNDS FOR THE PREVENTION OR TREATMENT OF CHRONIC PROSTATITIS<br/>[FR] UTILISATION DE COMPOSES DE VITAMINE D POUR LA PREVENTION OU LE TRAITEMENT DE LA PROSTATITE CHRONIQUE
  申请人：BIOXELL SPA

  公开号：WO2006035075A1

  公开（公告）日：2006-04-06

  The use of a vitamin D compound in the prevention or treatment of chronic prostatitis and related methods, pharmaceutical formulations and kits.

  维生素D化合物在慢性前列腺炎的预防或治疗中的使用，以及相关方法、药物配方和工具包。
• WO2006/51106
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2006/100285
  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.