methyl 1-O-<(R)-3-<4-(2,2-diphenylacetyl)piperazin-1-yl>-1-(quinolin-5-yloxy)-2-propyl>-2,3,4-tri-O-pivaloyl-β-D-glucuronate | 222054-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1-O-<(R)-3-<4-(2,2-diphenylacetyl)piperazin-1-yl>-1-(quinolin-5-yloxy)-2-propyl>-2,3,4-tri-O-pivaloyl-β-D-glucuronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[(2R)-1-[4-(2,2-diphenylacetyl)piperazin-1-yl]-3-quinolin-5-yloxypropan-2-yl]oxyoxane-2-carboxylate
• CAS: 222054-82-2
• 化学式: C₅₂H₆₅N₃O₁₂
• 分子量: 924.101
• InChiKey: LKOIQUOAZDTYLS-UGUQQJRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  67
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 1-O-<(R)-3-<4-(2,2-diphenylacetyl)piperazin-1-yl>-1-(quinolin-5-yloxy)-2-propyl>-2,3,4-tri-O-pivaloyl-β-D-glucuronate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以78.5%的产率得到1-O-<(R)-3-<4-(2,2-diphenylacetyl)piperazin-1-yl>-1-(quinolin-5-yloxy)-2-propyl>-β-D-glucuronic acid sodium salt
  参考文献：
  名称：

  Synthesis of glucuronides of multidrug resistance reversing drug MS-209

  摘要：

  We synthesized the glucuronides of MS-209 to identify the two main unknown metabolites in human urine. Reaction of MS-209 and glucuronyl trichloroacetimidate gave two beta-isomers, which were each glucuronate of (R)- and (S)-MS-209. These spectrum data were identical with the metabolites. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00056-6
• 作为产物：
  描述：

  methyl 1-bromo-1-deoxy-2,3,4-tri-O-pivaloyl-α-D-glucopyranuronate 在 三氟化硼乙醚 、 水 、 silver trifluoromethanesulfonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 硝基甲烷 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 methyl 1-O-<(R)-3-<4-(2,2-diphenylacetyl)piperazin-1-yl>-1-(quinolin-5-yloxy)-2-propyl>-2,3,4-tri-O-pivaloyl-β-D-glucuronate
  参考文献：
  名称：

  Synthesis of glucuronides of multidrug resistance reversing drug MS-209

  摘要：

  We synthesized the glucuronides of MS-209 to identify the two main unknown metabolites in human urine. Reaction of MS-209 and glucuronyl trichloroacetimidate gave two beta-isomers, which were each glucuronate of (R)- and (S)-MS-209. These spectrum data were identical with the metabolites. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00056-6