(2S,3S,4S,5R,6S)-6-(3-Allyloxycarbonyl-propylcarbamoyloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester | 168072-92-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S,4S,5R,6S)-6-(3-Allyloxycarbonyl-propylcarbamoyloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS: 168072-92-2
• 化学式: C₄₂H₄₅NO₁₀
• 分子量: 723.82
• InChiKey: UIKDMXWGDBLCSR-HRJWXXEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  53.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  127.85
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-6-(3-Allyloxycarbonyl-propylcarbamoyloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 在 吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(3-carboxy-propylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  β-Glucuronyl carbamate based pro-moieties designed for prodrugs in ADEPT

  摘要：

  A number of pro-moieties 8a - e designed for prodrug preparation have been synthesized (chart 2). The pro-moieties, containing a glucuronyl carbamate group linked to a spacer possessing a terminal carboxylic acid group, have been synthesized from isocyanates 6 and anomerically unprotected glucuronic acids 10 (chart 2). The requisite isocyanates had to be prepared using the Curtius rearrangement. Glucuronyl carbamates proved to be excellent substrates for human beta-glucuronidase. The pro-moieties 8a - e can be coupled to hydroxy- or amino group containing drugs. The resulting prodrugs are designed to be activated by beta-glucuronidase (chart 1) and to be used in ADEPT. Application is demonstrated with the synthesis of daunomycin prodrugs 12a - e (chart 3).

  DOI：

  10.1016/0040-4039(95)00049-i
• 作为产物：
  描述：

  5-(allyloxy)-5-oxopentanoic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 (2S,3S,4S,5R,6S)-6-(3-Allyloxycarbonyl-propylcarbamoyloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  β-Glucuronyl carbamate based pro-moieties designed for prodrugs in ADEPT

  摘要：

  A number of pro-moieties 8a - e designed for prodrug preparation have been synthesized (chart 2). The pro-moieties, containing a glucuronyl carbamate group linked to a spacer possessing a terminal carboxylic acid group, have been synthesized from isocyanates 6 and anomerically unprotected glucuronic acids 10 (chart 2). The requisite isocyanates had to be prepared using the Curtius rearrangement. Glucuronyl carbamates proved to be excellent substrates for human beta-glucuronidase. The pro-moieties 8a - e can be coupled to hydroxy- or amino group containing drugs. The resulting prodrugs are designed to be activated by beta-glucuronidase (chart 1) and to be used in ADEPT. Application is demonstrated with the synthesis of daunomycin prodrugs 12a - e (chart 3).

  DOI：

  10.1016/0040-4039(95)00049-i