2-[4-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester | 756488-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[4-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester
• CAS: 756488-29-6
• 化学式: C₄₃H₅₀O₁₀
• 分子量: 726.864
• InChiKey: NJXMVUPHQGSQLK-YRIQKYLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  118.98
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-[4-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester 在 Pearlman's catalyst 氢气 作用下， 以 水 、 叔丁醇 为溶剂， 以73%的产率得到2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester
  参考文献：
  名称：

  The β-glucuronyl-based prodrug strategy allows for its application on β-glucuronyl-platinum conjugates

  摘要：

  The use of platinum drugs in antitumour therapy is well established. An important drawback of these chemotherapeutics is the lack of selectivity for tumour cells, usually resulting in severe toxic side effects. A glucuronyl-platinum conjugate was designed and synthesised to test the compatibility of platinum compounds with beta-glucuronidase-based prodrug therapy. Instantaneous cleavage of the beta-glucuronic bond in the glucuronyl-platinum conjugate was observed upon addition of beta-glucuronidase resulting in Pt-II(dach)(4-hydroxybenzylmalonate) and glucuronic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.015
• 作为产物：
  描述：

  4-benzoyloxybenzyl bromide 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-[4-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester
  参考文献：
  名称：

  The β-glucuronyl-based prodrug strategy allows for its application on β-glucuronyl-platinum conjugates

  摘要：

  The use of platinum drugs in antitumour therapy is well established. An important drawback of these chemotherapeutics is the lack of selectivity for tumour cells, usually resulting in severe toxic side effects. A glucuronyl-platinum conjugate was designed and synthesised to test the compatibility of platinum compounds with beta-glucuronidase-based prodrug therapy. Instantaneous cleavage of the beta-glucuronic bond in the glucuronyl-platinum conjugate was observed upon addition of beta-glucuronidase resulting in Pt-II(dach)(4-hydroxybenzylmalonate) and glucuronic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.015