(8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(2S)-2-hydroxy-4-(methoxycarbonyl)-4-penten-1-yl]pregnane | 1076245-52-7

• 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: (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(2S)-2-hydroxy-4-(methoxycarbonyl)-4-penten-1-yl]pregnane
• CAS: 1076245-52-7
• 化学式: C₂₅H₄₆O₄Si
• 分子量: 438.723
• InChiKey: WAURIWVCJPTBLV-PZFYEKQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(2S)-2-hydroxy-4-(methoxycarbonyl)-4-penten-1-yl]pregnane 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以93%的产率得到(S)-5-((R)-2-((1R,3aR,4S,7aR)-7a-methyl-4-((triethylsilyl)oxy)octahydro-1H-inden-1-yl)propyl)-3-methylenedihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and biological properties of 2-methylene-19-nor-25-dehydro-1α-hydroxyvitamin D3-26,23-lactones—weak agonists

  摘要：

  In a continuing effort to explore the 2-methylene-1 alpha-hydroxy-19-norvitamin D-3 class of pharmacologically important vitamin D compounds, two novel 2-methylene-19-nor-25-dehydro-1 alpha-hydroxyvitamin D-3-26,23-lactones, GC-3 and HLV, were synthesized and biologically tested. Based on reports of similarly structured molecules, it was hypothesized that these compounds might act as antagonists, at least in vitro. The pathway designed to synthesize these compounds was based on two key steps: first, the Lythgoe-type Wittig-Horner coupling of Windaus-Grundmann-type ketone 18, with phosphine oxide 15, followed, later in the synthesis, by the Zn-mediated Reformasky-type allylation of aldehyde 20 with methylbromomethylacrylate 8. Our biological data show that neither compound has antagonistic activity but acts as weak agonists in vitro and in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.011
• 作为产物：
  描述：

  (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-(formylmethyl)pregnane 、 2-(溴甲基)丙烯酸甲酯 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以48%的产率得到(8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(2R)-2-hydroxy-4-(methoxycarbonyl)-4-penten-1-yl]pregnane
  参考文献：
  名称：

  Synthesis and biological properties of 2-methylene-19-nor-25-dehydro-1α-hydroxyvitamin D3-26,23-lactones—weak agonists

  摘要：

  In a continuing effort to explore the 2-methylene-1 alpha-hydroxy-19-norvitamin D-3 class of pharmacologically important vitamin D compounds, two novel 2-methylene-19-nor-25-dehydro-1 alpha-hydroxyvitamin D-3-26,23-lactones, GC-3 and HLV, were synthesized and biologically tested. Based on reports of similarly structured molecules, it was hypothesized that these compounds might act as antagonists, at least in vitro. The pathway designed to synthesize these compounds was based on two key steps: first, the Lythgoe-type Wittig-Horner coupling of Windaus-Grundmann-type ketone 18, with phosphine oxide 15, followed, later in the synthesis, by the Zn-mediated Reformasky-type allylation of aldehyde 20 with methylbromomethylacrylate 8. Our biological data show that neither compound has antagonistic activity but acts as weak agonists in vitro and in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.011