(3R,4R,5S)-4-(3-hydroxypropoxy)oct-1-en-7-yne-3,5-diol | 915160-26-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4R,5S)-4-(3-hydroxypropoxy)oct-1-en-7-yne-3,5-diol
• CAS: 915160-26-8
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: NXCJQNYRLSZHDV-VWYCJHECSA-N

物化性质

• 沸点：
  380.5±42.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-4-(3-hydroxypropoxy)oct-1-en-7-yne-3,5-diol 在 四(三苯基膦)钯 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of a 3-position diastereomer of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

  摘要：

  A 3-position diastereomer of 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 (ED-71, 2), 3-epi-ED-71 (4), was synthesized by the convergent method coupling the A-ring fragment (5) with the C/D-ring fragment (6). As the results of preliminary in vitro biological evaluation of 3-epi-ED-71 (4), the inhibition of parathyroid hormone secretion in bovine parathyroid cells and binding affinity to human recombinant vitamin D receptor and to human vitamin D binding protein in comparison with ED-71 (2), 1alpha,25-dihydroxyvitamin D3 (1,25(OH)2D3, 1), and 3-epi-1,25(OH)2D3 (3) are described.

  DOI：

  10.1016/j.bmc.2006.07.039
• 作为产物：
  描述：

  3-[(1S)-2-hydroxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-enyloxy]propyl pivalate 在 sodium hydroxide 、 正丁基锂 、 Novozyme 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 214.5h， 生成 (3R,4R,5S)-4-(3-hydroxypropoxy)oct-1-en-7-yne-3,5-diol
  参考文献：
  名称：

  Synthesis and evaluation of a 3-position diastereomer of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

  摘要：

  A 3-position diastereomer of 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 (ED-71, 2), 3-epi-ED-71 (4), was synthesized by the convergent method coupling the A-ring fragment (5) with the C/D-ring fragment (6). As the results of preliminary in vitro biological evaluation of 3-epi-ED-71 (4), the inhibition of parathyroid hormone secretion in bovine parathyroid cells and binding affinity to human recombinant vitamin D receptor and to human vitamin D binding protein in comparison with ED-71 (2), 1alpha,25-dihydroxyvitamin D3 (1,25(OH)2D3, 1), and 3-epi-1,25(OH)2D3 (3) are described.

  DOI：

  10.1016/j.bmc.2006.07.039

文献信息

• Synthesis and evaluation of a 3-position diastereomer of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)
  作者：Susumi Hatakeyama、Satoshi Nagashima、Naoko Imai、Keisuke Takahashi、Jun Ishihara、Atsuko Sugita、Takeshi Nihei、Hitoshi Saito、Fumiaki Takahashi、Noboru Kubodera

  DOI：10.1016/j.bmc.2006.07.039

  日期：2006.12

  A 3-position diastereomer of 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 (ED-71, 2), 3-epi-ED-71 (4), was synthesized by the convergent method coupling the A-ring fragment (5) with the C/D-ring fragment (6). As the results of preliminary in vitro biological evaluation of 3-epi-ED-71 (4), the inhibition of parathyroid hormone secretion in bovine parathyroid cells and binding affinity to human recombinant vitamin D receptor and to human vitamin D binding protein in comparison with ED-71 (2), 1alpha,25-dihydroxyvitamin D3 (1,25(OH)2D3, 1), and 3-epi-1,25(OH)2D3 (3) are described.