(1S,2S,6R,7R,9S)-2-[(tert-butyldimethylsilyl)oxy]-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methyl-9-{[methylthio(thiocarbonyl)]oxy}bicyclo[4.3.0]nonane | 1305339-98-3

• 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: (1S,2S,6R,7R,9S)-2-[(tert-butyldimethylsilyl)oxy]-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methyl-9-{[methylthio(thiocarbonyl)]oxy}bicyclo[4.3.0]nonane
• CAS: 1305339-98-3
• 化学式: C₂₈H₅₄O₄S₂Si
• 分子量: 546.952
• InChiKey: YBABGNHSVVRBSR-WYNGQYJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R,7R,9S)-2-[(tert-butyldimethylsilyl)oxy]-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methyl-9-{[methylthio(thiocarbonyl)]oxy}bicyclo[4.3.0]nonane 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 21.0h， 生成 (1R,2S,6R,7R)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]nonan-2-ol
  参考文献：
  名称：

  New C15-Substituted Active Vitamin D₃

  摘要：

  C15-Substituted 1 alpha,25-dihydroxyvitamin D-3 analogs were synthesized for the first time to investigate the effects of the modified CD-ring on biological activity concerning the agonistic positioning of helix-3 and helix-12 of the vitamin D receptor (VDR). X-ray cocrystallographic analysis proved that 0.6 angstrom shifts of the CD-ring and shrinking of the side chain were necessary to maintain the position of the 25-hydroxy group for proper interaction with helix-12. The 15-hydroxy-16-ene derivative showed higher binding affinity for hVDR than the natural hormone.

  DOI：

  10.1021/ol200828s
• 作为产物：
  描述：

  (1S,2S,6S,8R,9R)-2-[(tert-butyldimethylsilyl)oxy]-8,9-epoxy-6-methylbicyclo[4.3.0]nonan-7-one 在 正丁基锂 、 palladium on carbon 、 氢气 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 95.5h， 生成 (1S,2S,6R,7R,9S)-2-[(tert-butyldimethylsilyl)oxy]-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methyl-9-{[methylthio(thiocarbonyl)]oxy}bicyclo[4.3.0]nonane
  参考文献：
  名称：

  New C15-Substituted Active Vitamin D₃

  摘要：

  C15-Substituted 1 alpha,25-dihydroxyvitamin D-3 analogs were synthesized for the first time to investigate the effects of the modified CD-ring on biological activity concerning the agonistic positioning of helix-3 and helix-12 of the vitamin D receptor (VDR). X-ray cocrystallographic analysis proved that 0.6 angstrom shifts of the CD-ring and shrinking of the side chain were necessary to maintain the position of the 25-hydroxy group for proper interaction with helix-12. The 15-hydroxy-16-ene derivative showed higher binding affinity for hVDR than the natural hormone.

  DOI：

  10.1021/ol200828s