[1R,3aR,4S,7aR]-5(R,S)-benzenesulfonyl-6(S)-[4-(tert-butyldimethylsillanyloxy)-7a-methyl-octahydro-inden-1-yl]-2,10-dimethyl-undecane-2,3(R),10-triol | 792959-67-2

• 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,4S,7aR]-5(R,S)-benzenesulfonyl-6(S)-[4-(tert-butyldimethylsillanyloxy)-7a-methyl-octahydro-inden-1-yl]-2,10-dimethyl-undecane-2,3(R),10-triol
• 英文别名: [1R,3aR,4S,7aR]-6(S)-[4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-2,10-dimethyl-10-trimethylsilanyloxy-undecane-2,3(R)-diol；5-benzenesulfonyl-6(S)-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]-2,10-dimethylundecane-2,3(R),10-triol；(3R,6R)-6-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-5-(benzenesulfonyl)-2,10-dimethylundecane-2,3,10-triol
• CAS: 792959-67-2
• 化学式: C₃₅H₆₂O₆SSi
• 分子量: 639.025
• InChiKey: WLFSAHIHKININL-JBVTZBFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1R,3aR,4S,7aR]-5(R,S)-benzenesulfonyl-6(S)-[4-(tert-butyldimethylsillanyloxy)-7a-methyl-octahydro-inden-1-yl]-2,10-dimethyl-undecane-2,3(R),10-triol 在 甲醇 、 sodium-mercury amalgam (5%) 、 六氟合硅酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (3R,6S)-6-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydroinden-1-yl)-2,10-dimethylundecane-2,3,10-triol
  参考文献：
  名称：

  WO2006/100285

  摘要：

  公开号：
• 作为产物：
  描述：

  (2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate 在 正丁基锂 、 草酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.92h， 生成 [1R,3aR,4S,7aR]-5(R,S)-benzenesulfonyl-6(S)-[4-(tert-butyldimethylsillanyloxy)-7a-methyl-octahydro-inden-1-yl]-2,10-dimethyl-undecane-2,3(R),10-triol
  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.