methyl 3-N,4-O-di-allyloxycarbonyl-acosaminide | 452071-47-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-N,4-O-di-allyloxycarbonyl-acosaminide
• 英文别名: methyl 3-N,4-O-di-allyloxycarbonyl-2,3,6-trideoxy-3-amino-α-L-arabino-hexopyranoside
• CAS: 452071-47-5
• 化学式: C₁₅H₂₃NO₇
• 分子量: 329.35
• InChiKey: TYPPWPJDSQZXAB-RVMXOQNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3-N,4-O-di-allyloxycarbonyl-acosaminide 在 吡啶 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 4 A molecular sieve 作用下， 以 乙醚 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 7.0h， 生成 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity

  摘要：

  Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1-4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds. and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00411-4
• 作为产物：
  描述：

  甲基-alpha-L-葡糖胺 、 氯甲酸烯丙酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以70%的产率得到methyl 3-N,4-O-di-allyloxycarbonyl-acosaminide
  参考文献：
  名称：

  Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity

  摘要：

  Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1-4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds. and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00411-4