(2R,3R,4S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-3,4-dipivaloxy-1,2-diol | 930767-45-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-3,4-dipivaloxy-1,2-diol
• CAS: 930767-45-6
• 化学式: C₁₉H₃₄O₈
• 分子量: 390.474
• InChiKey: UKLYDHREOVGRJM-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-3,4-dipivaloxy-1,2-diol 在 乙酸酐 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (3S,4S)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dipivaloxy-1-butene
  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：

  三甲基乙酰氯 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 44.0h， 生成 (2R,3R,4S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-3,4-dipivaloxy-1,2-diol
  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