2α-(3-hydroxypropoxy)-1α,25-dihydroxyvitamin D₃

• 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: 2α-(3-hydroxypropoxy)-1α,25-dihydroxyvitamin D₃
• 英文别名: 2α-(-hydroxypropoxy)-1α,25-dihydroxyvitamin D₃；2α-(3-hydroxypropoxy)-1α,25(OH)₂D₃；1alpha,25-dihydroxy-2alpha-(3-hydroxypropoxy)vitamin D3；(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-(3-hydroxypropoxy)-4-methylidenecyclohexane-1,3-diol
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: FZEXGDDBXLBRTD-VCBASKJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 三氟化硼乙醚 、 potassium tert-butylate 、 四丁基氟化铵 、 sodium methylate 、 sodium cyanoborohydride 、 potassium carbonate 、 三乙胺 、 barium carbonate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 115.92h， 生成 2α-(3-hydroxypropoxy)-1α,25-dihydroxyvitamin D₃
  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

文献信息

• A Concise and Efficient Route to 2α-(ω-Hydroxyalkoxy)-1α,25-dihydroxyvitamin D₃:  Remarkably High Affinity to Vitamin D Receptor¹
  作者：Atsushi Kittaka、Yoshitomo Suhara、Hitoshi Takayanagi、Toshie Fujishima、Masaaki Kurihara、Hiroaki Takayama

  DOI：10.1021/ol006222j

  日期：2000.8.1

  [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.