propan-2-yl (2R,3S)-2-(1,3-benzodioxol-5-yl)-3-[(4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoate | 1226976-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: propan-2-yl (2R,3S)-2-(1,3-benzodioxol-5-yl)-3-[(4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoate
• CAS: 1226976-36-8
• 化学式: C₂₅H₄₀O₈Si
• 分子量: 496.673
• InChiKey: OXKDYDTZSOOLPE-LNRXMEIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  propan-2-yl (2R,3S)-2-(1,3-benzodioxol-5-yl)-3-[(4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoate 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以96%的产率得到
  参考文献：
  名称：

  Potent and selective inhibition of human cytochrome P450 3A4 by seco-pancratistatin structural analogs

  摘要：

  seco-Derivatives of the anticancer agent pancratistatin bearing the 2S,3S,4S,5S configuration were accessed via a novel, highly diastereoselective anti-aldol reaction. Structure-activity relationships reveal important insights into the seco-pancratistatin pharmacophore as a potent and selective inhibitor of human cytochrome P450 3A4 (CYP3A4), and highlight features of concern in advancing a potent, selective anticancer agent in the pancratistatin series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.157
• 作为产物：
  描述：

  isopropyl 2-(3,4-methylenedioxyphenyl)acetate 、 (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到propan-2-yl (2R,3S)-2-(1,3-benzodioxol-5-yl)-3-[(4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoate
  参考文献：
  名称：

  Potent and selective inhibition of human cytochrome P450 3A4 by seco-pancratistatin structural analogs

  摘要：

  seco-Derivatives of the anticancer agent pancratistatin bearing the 2S,3S,4S,5S configuration were accessed via a novel, highly diastereoselective anti-aldol reaction. Structure-activity relationships reveal important insights into the seco-pancratistatin pharmacophore as a potent and selective inhibitor of human cytochrome P450 3A4 (CYP3A4), and highlight features of concern in advancing a potent, selective anticancer agent in the pancratistatin series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.157