18-acetoxyvitamin D3 | 140927-91-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 18-acetoxyvitamin D3
• 英文别名: 18-acetoxy-vitamin D3/18-acetoxy-cholecalciferol；[(3R,3aS,7E,7aS)-7-[(2Z)-2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-3-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7a-hexahydro-1H-inden-3a-yl]methyl acetate
• CAS: 140927-91-9
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: GKWGCITYEOHSED-HKCRWRSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Grundmann's alcohol 在 吡啶 、 lead(IV) acetate 、 ruthenium trichloride 、 sodium periodate 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙腈 、 苯 为溶剂， 反应 78.67h， 生成 18-acetoxyvitamin D3
  参考文献：
  名称：

  Studies of vitamin D (calciferol) and its analogs. 41. 18-Substituted derivatives of vitamin D: 18-acetoxy-1.alpha.,25-dihydroxyvitamin D3 and related analogs

  摘要：

  The bridged ether 6, produced via light-induced lead tetraacetate oxidation of Grundmann's alcohol 5, was transformed in three to four steps to the CD-ring ketones 9b and 10 which were then transformed via Homer-Wittig coupling to the 18-acetoxy analogues of vitamin D3, 25-hydroxyvitamin D3, 1-alpha,25-dihydroxyvitamin D3, and 1-alpha-hydroxyvitamin D3 (4a-d, respectively). The biological evaluation of 4a-d in terms of their ability to elicit intestinal calcium absorption and bone calcium mobilization in vivo in the chick is reported. These vitamin D analogues, the first in this steroid series modified at the C-18 position, are nearly devoid of activity. In vitro data for 4a-d in terms of their ability to bind to the chick intestinal receptor as compared to the natural hormone 1-alpha,25-dihydroxyvitamin D3, parallels the in vivo data.

  DOI：

  10.1021/jo00037a046