3-[(1S,2S)-2-hydroxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-enyloxy]propyl pivalate | 957255-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(1S,2S)-2-hydroxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-enyloxy]propyl pivalate
• 英文别名: 3-[(1S,2S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxybut-3-enoxy]propyl 2,2-dimethylpropanoate
• CAS: 957255-02-6
• 化学式: C₁₇H₃₀O₆
• 分子量: 330.422
• InChiKey: UYSZSQVRRIGWPG-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(1S,2S)-2-hydroxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-enyloxy]propyl pivalate 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以80%的产率得到3-[(1S,2S)-2-acetoxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-enyloxy]propyl pivalate
  参考文献：
  名称：

  Synthesis of 1,3-DIEPI-ED-71, a biologically important diastereomer of 1α,25-Dihydroxy-2β-(3-hydroxypropoxy)vitamin D3(ED-71)

  摘要：

  The synthesis of biologically important 1,3-diepi-ED-71, a diastereomer of 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71) at the 1-position and 3-position of the A-ring using Trost's coupling methodology is described.

  DOI：

  10.1016/s0385-5414(07)81102-6
• 作为产物：
  描述：

  [(S)-2-hydroxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]propyl pivalate 在 草酰氯 、 Novozyme 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 171.0h， 生成 3-[(1S,2S)-2-hydroxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-enyloxy]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

文献信息

• Synthesis of 1,3-DIEPI-ED-71, a biologically important diastereomer of 1α,25-Dihydroxy-2β-(3-hydroxypropoxy)vitamin D3(ED-71)
  作者：A FUJIYAMAA、M KANEKO、K TAKAHASHI、J ISHIHARA、S HATAKEYAMA、N KUBODER

  DOI：10.1016/s0385-5414(07)81102-6

  日期：2007.10.1

  The synthesis of biologically important 1,3-diepi-ED-71, a diastereomer of 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71) at the 1-position and 3-position of the A-ring using Trost's coupling methodology is described.
• 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.