(6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3R,4S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[4-[tert-butyl(dimethyl)silyl]oxybutoxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptan-2-ol | 794516-15-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3R,4S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[4-[tert-butyl(dimethyl)silyl]oxybutoxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptan-2-ol
• CAS: 794516-15-7
• 化学式: C₄₉H₉₄O₅Si₃
• 分子量: 847.539
• InChiKey: VYSRIONSJFGNDJ-JGWYBYIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.56
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3R,4S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[4-[tert-butyl(dimethyl)silyl]oxybutoxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptan-2-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(1R,2S,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-(4-hydroxybutoxy)-4-methylidenecyclohexane-1,3-diol
  参考文献：
  名称：

  A Concise and Efficient Route to 2α-(ω-Hydroxyalkoxy)-1α,25-dihydroxyvitamin D₃:  Remarkably High Affinity to Vitamin D Receptor¹

  摘要：

  [GRAPHICS]A convenient and potentially valuable synthetic approach to the novel 2 alpha-functionalized 1 alpha,25-dihydroxyvitamin D-3 [1 alpha,25(OH)(2)D-3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2 alpha-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25(OH)(2)D-3 derivatives, la and Ib showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.

  DOI：

  10.1021/ol006222j
• 作为产物：
  描述：

  (R)-2-{(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[4-(tert-butyl-dimethyl-silanyloxy)-butoxy]-but-3-enyl}-oxirane 在 2,6-二甲基吡啶 、 四(三苯基膦)钯 、 正丁基锂 、 三氟化硼乙醚 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3R,4S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[4-[tert-butyl(dimethyl)silyl]oxybutoxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptan-2-ol
  参考文献：
  名称：

  A Concise and Efficient Route to 2α-(ω-Hydroxyalkoxy)-1α,25-dihydroxyvitamin D₃:  Remarkably High Affinity to Vitamin D Receptor¹

  摘要：

  [GRAPHICS]A convenient and potentially valuable synthetic approach to the novel 2 alpha-functionalized 1 alpha,25-dihydroxyvitamin D-3 [1 alpha,25(OH)(2)D-3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2 alpha-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25(OH)(2)D-3 derivatives, la and Ib showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.

  DOI：

  10.1021/ol006222j