(20R,24R)-3β-(tert-Butyldimethylsilyloxy)cholesta-5,7-diene-24,25-diol | 146237-13-0

• 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: (20R,24R)-3β-(tert-Butyldimethylsilyloxy)cholesta-5,7-diene-24,25-diol
• 英文别名: (24R)-3β-(tert-butyldimethylsilyloxy)cholesta-5,7-diene-24,25-diol；(3R,6R)-6-[(3S,9S,10R,13R,14R,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-2,3-diol
• CAS: 146237-13-0
• 化学式: C₃₃H₅₈O₃Si
• 分子量: 530.907
• InChiKey: BNKDRNAVOIJQPP-OPCLSYGASA-N

物化性质

• 沸点：
  590.4±50.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20R,24R)-3β-(tert-Butyldimethylsilyloxy)cholesta-5,7-diene-24,25-diol 在 吡啶 、 sodium hydroxide 、 四丁基氟化铵 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 57.5h， 生成 (5Z,7E)-(3S,24R)-24,25-dihydroxy-9,10-secocholesta-5,7,10(19)-trien-3β-yl β-D-glycopyranuronic acid
  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：

  (2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate 在 disodium hydrogenphosphate 、 正丁基锂 、 sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.5h， 生成 (20R,24R)-3β-(tert-Butyldimethylsilyloxy)cholesta-5,7-diene-24,25-diol
  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

文献信息

• Scherlitz-Hofmann, Ina; Boessneck, Ulrich; Schoenecker, Bruno, Liebigs Annalen, 1996, # 2, p. 217 - 222
  作者：Scherlitz-Hofmann, Ina、Boessneck, Ulrich、Schoenecker, Bruno

  DOI：——

  日期：——
• In vitro and in vivo glucuronidation of 24,25-dihydroxyvitamin D3
  作者：Tatsuya Higashi、Maki Horike、Ryuta Kikuchi、Kazutake Shimada

  DOI：10.1016/s0039-128x(99)00057-4

  日期：1999.10

  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.