4-O-[(4R,4aR,7S,7aR,12bS)-7-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] 1-O-[(4R,4aR,7S,7aR,12bS)-3-methyl-7-[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] benzene-1,4-dicarboxylate | 1333039-07-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 4-O-[(4R,4aR,7S,7aR,12bS)-7-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] 1-O-[(4R,4aR,7S,7aR,12bS)-3-methyl-7-[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] benzene-1,4-dicarboxylate
• CAS: 1333039-07-8
• 化学式: C₅₇H₅₈N₂O₁₈
• 分子量: 1059.09
• InChiKey: WRZGYUIBDHWDSW-QHWVEFDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  77
• 可旋转键数：
  18
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  228
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  di(morphin-3-yl) terephthalate 、 3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 在 三氟甲磺酸三甲基硅酯 作用下， 以 氯苯 为溶剂， 反应 0.5h， 生成 di(6-O-acetylmorphin-3-yl) terephthalate 、 4-O-[(4R,4aR,7S,7aR,12bS)-7-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] 1-O-[(4R,4aR,7S,7aR,12bS)-3-methyl-7-[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] benzene-1,4-dicarboxylate 、 bis[(4R,4aR,7S,7aR,12bS)-3-methyl-7-[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] benzene-1,4-dicarboxylate
  参考文献：
  名称：

  New approach in the synthesis of M6G

  摘要：

  Morphine-6-glucuronide (M6G) is the primarily active metabolite of morphine, produced endogenously by the UGT enzyme, which displays analgesic activity. For this reason, M6G is a promising drug candidate for the treatment of severe pain. We described herein a new, efficient and scalable synthesis of M6G using dimorphinic derivatives. This preparation of M6G could be performed on multigram scale with good yield and high purity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.011