(1S,2R,5R,6R,9R,10R,11R,12R,13R,15S)-12-(2-hydroxyethoxy)-6,10-dimethyl-5-[(2R)-6-methyl-6-triethylsilyloxyheptan-2-yl]-18-phenyl-11,13-bis(triethylsilyloxy)-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione | 246237-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,2R,5R,6R,9R,10R,11R,12R,13R,15S)-12-(2-hydroxyethoxy)-6,10-dimethyl-5-[(2R)-6-methyl-6-triethylsilyloxyheptan-2-yl]-18-phenyl-11,13-bis(triethylsilyloxy)-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione
• CAS: 246237-58-1
• 化学式: C₅₅H₉₅N₃O₇Si₃
• 分子量: 994.632
• InChiKey: SSJBNOMDZHCZQO-BMZKWCSESA-N

物化性质

• 沸点：
  831.2±75.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.39
• 重原子数：
  68.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  106.08
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,6R,9R,10R,11R,12R,13R,15S)-12-(2-hydroxyethoxy)-6,10-dimethyl-5-[(2R)-6-methyl-6-triethylsilyloxyheptan-2-yl]-18-phenyl-11,13-bis(triethylsilyloxy)-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione 在 咪唑 、 盐酸 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 14.36h， 生成 2β-(2-methoxycarbonylethyloxy)-1α,3β,25-trihydroxy-9,10-secocholesta-5,7,10(19)-triene
  参考文献：
  名称：

  Synthesis of putative metabolites of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

  摘要：

  1 alpha,25-Dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71), an analog of active vitamin D-3, 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3] is under phase III clinical trials in Japan for the treatment of osteoporosis and bone fracture prevention. Since ED-71 has a substituent at the 2 beta-position of the A-ring, it is recognized that the metabolic pathway of ED-71 might be more complicated than 1,25(OH)(2)D-3 because of metabolism at the 2 beta-position substituent in addition to the inherent metabolism of the side chain. To clarify the metabolism of hydroxypropoxy substituent of the 2 beta-positon and a combination of metabolism between side chain and 2 beta-positon, four putative metabolites of ED-71 have been prepared as authentic samples. The metabolites at the 2 beta-positon, the methyl ester derivative considered as an ester standard of the oxidized metabolite and the tetraol derivative as the truncated metabolite were synthesized from alpha-epoxide, a key intermediate of ED-71 synthesis. The combination metabolites between side chain and 2 beta-positon, the 24(S)- and 24(R)-pentaols were synthesized using Trost's convergent method. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.11.001
• 作为产物：
  描述：

  三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 、 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (1S,2R,5R,6R,9R,10R,11R,12R,13R,15S)-12-(2-hydroxyethoxy)-6,10-dimethyl-5-[(2R)-6-methyl-6-triethylsilyloxyheptan-2-yl]-18-phenyl-11,13-bis(triethylsilyloxy)-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione
  参考文献：
  名称：

  Synthesis of putative metabolites of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

  摘要：

  1 alpha,25-Dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71), an analog of active vitamin D-3, 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3] is under phase III clinical trials in Japan for the treatment of osteoporosis and bone fracture prevention. Since ED-71 has a substituent at the 2 beta-position of the A-ring, it is recognized that the metabolic pathway of ED-71 might be more complicated than 1,25(OH)(2)D-3 because of metabolism at the 2 beta-position substituent in addition to the inherent metabolism of the side chain. To clarify the metabolism of hydroxypropoxy substituent of the 2 beta-positon and a combination of metabolism between side chain and 2 beta-positon, four putative metabolites of ED-71 have been prepared as authentic samples. The metabolites at the 2 beta-positon, the methyl ester derivative considered as an ester standard of the oxidized metabolite and the tetraol derivative as the truncated metabolite were synthesized from alpha-epoxide, a key intermediate of ED-71 synthesis. The combination metabolites between side chain and 2 beta-positon, the 24(S)- and 24(R)-pentaols were synthesized using Trost's convergent method. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.11.001