3-[(2S,3S,4R)-4-acetoxy-1,2-dihydroxyhex-5-en-3-yloxy]propyl pivalate | 915160-24-6

• 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: 3-[(2S,3S,4R)-4-acetoxy-1,2-dihydroxyhex-5-en-3-yloxy]propyl pivalate
• CAS: 915160-24-6
• 化学式: C₁₆H₂₈O₇
• 分子量: 332.394
• InChiKey: LDGRXCHJEFKACF-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-[(2S,3S,4R)-4-acetoxy-1,2-dihydroxyhex-5-en-3-yloxy]propyl pivalate 在 sodium hydroxide 、 正丁基锂 、 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 24.5h， 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
• 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 Novozyme 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 190.0h， 生成 3-[(2S,3S,4R)-4-acetoxy-1,2-dihydroxyhex-5-en-3-yloxy]propyl pivalate
  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