(1S,5S,6S,7S)-5-[(tert-butyldimethylsilyl)oxy]-9-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-1-methylbicyclo[4.3.0]non-8-en-7-ol | 1181662-09-8

• 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,5S,6S,7S)-5-[(tert-butyldimethylsilyl)oxy]-9-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-1-methylbicyclo[4.3.0]non-8-en-7-ol
• 英文别名: (1S,3aS,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-3-[(2R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-3a-methyl-1,4,5,6,7,7a-hexahydroinden-1-ol
• CAS: 1181662-09-8
• 化学式: C₂₆H₅₀O₄Si
• 分子量: 454.766
• InChiKey: DASQBQVBSCURRM-PHDUCBFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5S,6S,7S)-5-[(tert-butyldimethylsilyl)oxy]-9-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-1-methylbicyclo[4.3.0]non-8-en-7-ol 在 偶氮二异丁腈 、 palladium on carbon 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 70.5h， 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：

  (1R,2S,6S)-7-acetoxy-2-[(tert-butyldimethylsilyl)oxy]-6-methylbicyclo[4.3.0]non-7-ene 在 正丁基锂 、 四丙基高钌酸铵 、 烯丙基甲基碳酸酯 、 三正丁基甲氧基锡 、 palladium diacetate 、 二异丁基氢化铝 、 magnesium 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 54.17h， 生成 (1S,5S,6S,7S)-5-[(tert-butyldimethylsilyl)oxy]-9-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-1-methylbicyclo[4.3.0]non-8-en-7-ol 、 (1S,5S,6S,7S)-5-[(tert-butyldimethylsilyl)oxy]-9-[(S)-6-(methoxymethoxy)-6-methylheptan-2-yl]-1-methylbicyclo[4.3.0]non-8-en-7-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