ethyl (5R)-2,2-difluoro-3-hydroxy-5-((1R,3aR,4S,7aR)-7a-methyl-4-((triethylsilyl)oxy)octahydro-1H-inden-1-yl)hexanoate | 891557-44-1

• 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: ethyl (5R)-2,2-difluoro-3-hydroxy-5-((1R,3aR,4S,7aR)-7a-methyl-4-((triethylsilyl)oxy)octahydro-1H-inden-1-yl)hexanoate
• CAS: 891557-44-1
• 化学式: C₂₄H₄₄F₂O₄Si
• 分子量: 462.693
• InChiKey: NAEKPURTPJFZEO-GEAPDXGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 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：

  ethyl (5R)-2,2-difluoro-3-hydroxy-5-((1R,3aR,4S,7aR)-7a-methyl-4-((triethylsilyl)oxy)octahydro-1H-inden-1-yl)hexanoate 、 硫代氯甲酸苯酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以90%的产率得到ethyl (5R)-2,2-difluoro-5-((1R,3aR,4S,7aR)-7a-methyl-4-((triethylsilyl)oxy)octahydro-1H-inden-1-yl)-3-((phenoxycarbonothioyl)oxy)hexanoate
  参考文献：
  名称：

  WO2006/74227

  摘要：

  公开号：
• 作为产物：
  描述：

  (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-(formylmethyl)pregnane 、 bromozinc(1+),ethyl 2,2-difluoroacetate 以 四氢呋喃 为溶剂， 反应 0.33h， 以62%的产率得到ethyl (5R)-2,2-difluoro-3-hydroxy-5-((1R,3aR,4S,7aR)-7a-methyl-4-((triethylsilyl)oxy)octahydro-1H-inden-1-yl)hexanoate
  参考文献：
  名称：

  WO2006/74227

  摘要：

  公开号：

文献信息

• A Methylene Group on C-2 of 24,24-Difluoro-19-nor-1α,25-dihydroxyvitamin D₃ Markedly Increases Bone Calcium Mobilization in Vivo
  作者：Agnieszka Flores、Ilaria Massarelli、James B. Thoden、Lori A. Plum、Hector F. DeLuca

  DOI：10.1021/acs.jmedchem.5b01564

  日期：2015.12.24

  Four side chain fluorinated analogues of 1 alpha,25-dihydroxy-19-norvitamin D have been prepared in convergent syntheses using the Wittig-Homer reaction as a key step. Structures and absolute configurations of analogues 3 and 5 were confirmed by X-ray crystallography. All analogues showed high potency in HL-60 cell differentiation and vitamin D-24-hydroxylase (24-OHase) transcription as compared to 1 alpha,25-dihydroxyvitamin D-3 (1). Most important is that all of the 20S-configured derivatives (4 and 6) had high bone mobilizing activity in vivo. However, in the 20R series, a 2-methylene group was required for high bone mobilizing activity. A change in positioning of the 20R molecule in the vitamin D receptor when the 2-methylene group is present may provide new insight into the molecular basis of bone calcium mobilization induced by vitamin D.