methyl {[(24R)-3β-acetoxycholesta-5,7-dien-25-ol-24-yl]-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate | 203736-96-3

• 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: methyl {[(24R)-3β-acetoxycholesta-5,7-dien-25-ol-24-yl]-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate
• CAS: 203736-96-3
• 化学式: C₄₂H₆₂O₁₃
• 分子量: 774.946
• InChiKey: BCQLSPFGYZFCNK-IFSQGEKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  55.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  170.19
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl {[(24R)-3β-acetoxycholesta-5,7-dien-25-ol-24-yl]-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 以 乙醚 、 二氯甲烷 、 乙醇 为溶剂， 反应 27.5h， 以13.7%的产率得到methyl {[(5Z,7E)-(3S,24R)-3-acetoxy-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-24-yl]-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate
  参考文献：
  名称：

  In vitro and in vivo glucuronidation of 24,25-dihydroxyvitamin D3

  摘要：

  Glucuronidation of 24,25-dihydroxyvitamin D-3 has been investigated in in vitro and in vivo experiments. Three positional isomers of 24,25-dihydroxyvitamin D-3 monoglucuronide were synthesized from 24,25-dihydroxyprovitamin D-3 derivatives with Koenigs-Knorr reaction and used as standard samples. In the presence of the rat liver microsomal fraction and uridine-5'-diphosphoglucuronic acid, 24,25-dihydroxyvitamin D-3 gave 3- and 24-glucuronides as the main products in almost equal amounts, but only a small amount of the corresponding 25-glucuronide was obtained. 24,25-Dihydroxyvitamin D-3 monoglucuronide was deconjugated with rat intestine homogenate, which indicated the entero-hepatic circulation of 24,25-dihydroxyvitamin D-3. After the administration of 24,25-dihydroxyvitamin D-3 to rats, its 3- and 24-glucuronides were identified from the bile as inferred from the in vitro experiment. However, the in vivo glucuronidation occurred at the 24-position in preference to the 3-position, and the corresponding 25-glucuronide was not detected. These glucuronides were identified in comparison with standard samples based on their chromatographic behavior during high-performance liquid chromatography and data obtained from liquid chromatography-electrospray ionization-mass spectrometry, which was helpful in identifying these compounds. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00057-4
• 作为产物：
  描述：

  (24R)-24-(tert-butyldimethylsilyloxy)-25-hydroxycholesta-5,7-diene-3β-yl acetate 在 四丁基氟化铵 、 silver carbonate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 5.5h， 生成 methyl {[(24R)-3β-acetoxycholesta-5,7-dien-25-ol-24-yl]-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate
  参考文献：
  名称：

  In vitro and in vivo glucuronidation of 24,25-dihydroxyvitamin D3

  摘要：

  Glucuronidation of 24,25-dihydroxyvitamin D-3 has been investigated in in vitro and in vivo experiments. Three positional isomers of 24,25-dihydroxyvitamin D-3 monoglucuronide were synthesized from 24,25-dihydroxyprovitamin D-3 derivatives with Koenigs-Knorr reaction and used as standard samples. In the presence of the rat liver microsomal fraction and uridine-5'-diphosphoglucuronic acid, 24,25-dihydroxyvitamin D-3 gave 3- and 24-glucuronides as the main products in almost equal amounts, but only a small amount of the corresponding 25-glucuronide was obtained. 24,25-Dihydroxyvitamin D-3 monoglucuronide was deconjugated with rat intestine homogenate, which indicated the entero-hepatic circulation of 24,25-dihydroxyvitamin D-3. After the administration of 24,25-dihydroxyvitamin D-3 to rats, its 3- and 24-glucuronides were identified from the bile as inferred from the in vitro experiment. However, the in vivo glucuronidation occurred at the 24-position in preference to the 3-position, and the corresponding 25-glucuronide was not detected. These glucuronides were identified in comparison with standard samples based on their chromatographic behavior during high-performance liquid chromatography and data obtained from liquid chromatography-electrospray ionization-mass spectrometry, which was helpful in identifying these compounds. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00057-4