N-methyl-N-{4-[allyl 2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosiduronate]-3-nitrobenzyloxycarbonyl}-2-aminoethanol | 901778-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-N-{4-[allyl 2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosiduronate]-3-nitrobenzyloxycarbonyl}-2-aminoethanol
• CAS: 901778-59-4
• 化学式: C₃₈H₆₈N₂O₁₂Si₃
• 分子量: 829.221
• InChiKey: PVSVTMDUXRAUME-FVRGGSDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  55.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  165.36
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-methyl-N-{4-[allyl 2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosiduronate]-3-nitrobenzyloxycarbonyl}-2-aminoethanol 、 N,N'-二琥珀酰亚胺基碳酸酯 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到1-{N-methyl-N-[4-(allyl 2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosiduronate)-3-nitrobenzyloxycarbonyl]-2-aminoethoxycarbonyl}pyrrolidine-2,5-dione
  参考文献：
  名称：

  New Taxol® (paclitaxel) prodrugs designed for ADEPT and PMT strategies in cancer chemotherapy

  摘要：

  Two new glucuronide paclitaxel prodrugs have been synthesized. Linked to the 2'-OH of the drug by a carbonate function, they include a self-immolative spacer bearing an arylnitro or arylamino group between the drug and the glucuronic acid residue. Both prodrugs were well detoxified and easily cleaved in the presence of beta-D-glucuronidase with fast removal of the spacer, releasing paclitaxel. The arylamino spacer-containing prodrug, more stable than the corresponding nitro analogue, was selected for further studies.

  DOI：

  10.1016/j.bmc.2006.03.002
• 作为产物：
  描述：

  allyl {(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid}uronate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-methyl-N-{4-[allyl 2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosiduronate]-3-nitrobenzyloxycarbonyl}-2-aminoethanol
  参考文献：
  名称：

  New Taxol® (paclitaxel) prodrugs designed for ADEPT and PMT strategies in cancer chemotherapy

  摘要：

  Two new glucuronide paclitaxel prodrugs have been synthesized. Linked to the 2'-OH of the drug by a carbonate function, they include a self-immolative spacer bearing an arylnitro or arylamino group between the drug and the glucuronic acid residue. Both prodrugs were well detoxified and easily cleaved in the presence of beta-D-glucuronidase with fast removal of the spacer, releasing paclitaxel. The arylamino spacer-containing prodrug, more stable than the corresponding nitro analogue, was selected for further studies.

  DOI：

  10.1016/j.bmc.2006.03.002