methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-methoxycarbonyloxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-triacetyloxyoxane-2-carboxylate | 330823-63-7

• 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)-9-methoxycarbonyloxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-triacetyloxyoxane-2-carboxylate
• CAS: 330823-63-7
• 化学式: C₃₂H₃₉NO₁₄
• 分子量: 661.66
• InChiKey: KPROEFNHUDIBTC-FUCFKQMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-methoxycarbonyloxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-triacetyloxyoxane-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以85%的产率得到Dihydromorphine 6-β-D-glucuronide
  参考文献：
  名称：

  Selective synthesis of both isomers of morphine 6-β-d-glucuronide and their analogs

  摘要：

  A stereoselective synthesis of both isomers of the pharmaceutically important morphine 6-beta -D-glucuronide (M6G) and its analogs was developed. The method is based on the use of ZnBr2 for the key coupling reaction. It was shown that the alpha/beta stereoselectivity of the reaction can he directed and controlled by the amount of ZnBr2. This paper describes the synthesis, analysis and characterization of the Lu-isomer of M6C, useful as a reference marker for testing purity and stability of the morphine 6-beta -D-glucuronide (M6G). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01080-2
• 作为产物：
  描述：

  双氢吗啡 在 3 A molecular sieve 、 碳酸氢钠 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.0h， 生成 methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-methoxycarbonyloxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-triacetyloxyoxane-2-carboxylate
  参考文献：
  名称：

  Selective synthesis of both isomers of morphine 6-β-d-glucuronide and their analogs

  摘要：

  A stereoselective synthesis of both isomers of the pharmaceutically important morphine 6-beta -D-glucuronide (M6G) and its analogs was developed. The method is based on the use of ZnBr2 for the key coupling reaction. It was shown that the alpha/beta stereoselectivity of the reaction can he directed and controlled by the amount of ZnBr2. This paper describes the synthesis, analysis and characterization of the Lu-isomer of M6C, useful as a reference marker for testing purity and stability of the morphine 6-beta -D-glucuronide (M6G). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01080-2