(2S,3S,4R,5S,6S)-2-Bromomethyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-methoxy-tetrahydro-pyran | 299410-83-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6S)-2-Bromomethyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-methoxy-tetrahydro-pyran
• CAS: 299410-83-6
• 化学式: C₂₇H₅₉BrO₆Si₃
• 分子量: 643.922
• InChiKey: DTXISYBMEGEILP-VDLPQLTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6S)-2-Bromomethyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-methoxy-tetrahydro-pyran 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium cyanoborohydride 、 potassium carbonate 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 0.75h， 生成 (R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-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
• 作为产物：
  描述：

  methyl 4-O-benzoyl-6-bromo-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-6-deoxy-α-D-altropyranoside 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S,4R,5S,6S)-2-Bromomethyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-methoxy-tetrahydro-pyran
  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