allyl {(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid}uronate | 704885-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl {(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid}uronate
• CAS: 704885-33-6
• 化学式: C₃₄H₆₁NO₁₀Si₃
• 分子量: 728.116
• InChiKey: AZTNYZPSSKMSOT-WCDZDMCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  135.82
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 titanium(IV) isopropylate 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 allyl {(2-nitro-4-hydroxymethylphenyl)-2,3,4-tri-(O-tert-butyldimethylsilyl)-β-D-glucopyranosid}uronate
  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