methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-3-methyl-9-phenylmethoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-tris(2-methylpropanoyloxy)oxane-2-carboxylate | 286465-18-7

• 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: methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-3-methyl-9-phenylmethoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-tris(2-methylpropanoyloxy)oxane-2-carboxylate
• CAS: 286465-18-7
• 化学式: C₄₃H₅₃NO₁₂
• 分子量: 775.893
• InChiKey: VCPQUPDOQKKNAY-RCKAGJBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  56.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  145.36
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-3-methyl-9-phenylmethoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-tris(2-methylpropanoyloxy)oxane-2-carboxylate 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 以66%的产率得到3-O-benzylmorphine-6-glucuronide
  参考文献：
  名称：

  The enzymatic glucuronidation of 3-O-protected morphine—a new route to 7,8-dihydromorphine-6-glucuronide

  摘要：

  The selective enzymatic glucuronidation of the 6-position of morphine was probed by the glucuronidation of a series of 3-O-protected morphine derivatives. 3-O-Benzylmorphine 5 was converted to the corresponding 3-O-benzylmorphine-6-glucuronide 8 by human liver microsomes. The identity of 8 was confirmed by independent chemical synthesis. The glucuronide 8 was subsequently converted to 7,8-dihydromorphine-6-glucuronide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00582-0
• 作为产物：
  描述：

  甲基(5xi)-2,3,4-三-O-异丁酰基-1-O-(2,2,2-三氯亚氨代乙酰)-alpha-D-来苏-吡喃己糖酸酯 、 3-O-苄吗啉 在 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 以48%的产率得到methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-3-methyl-9-phenylmethoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-tris(2-methylpropanoyloxy)oxane-2-carboxylate
  参考文献：
  名称：

  The enzymatic glucuronidation of 3-O-protected morphine—a new route to 7,8-dihydromorphine-6-glucuronide

  摘要：

  The selective enzymatic glucuronidation of the 6-position of morphine was probed by the glucuronidation of a series of 3-O-protected morphine derivatives. 3-O-Benzylmorphine 5 was converted to the corresponding 3-O-benzylmorphine-6-glucuronide 8 by human liver microsomes. The identity of 8 was confirmed by independent chemical synthesis. The glucuronide 8 was subsequently converted to 7,8-dihydromorphine-6-glucuronide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00582-0