methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-benzoyloxy-3-methyl-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

• 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-benzoyloxy-3-methyl-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
• 化学式: C₄₃H₅₁NO₁₃
• 分子量: 789.877
• InChiKey: PBJATZONEFXEBN-BIVYJAPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-benzoyloxy-3-methyl-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 甲醇 为溶剂， 生成 甲醇:水(1:1)测试标样(吗啡-6-Β-D-葡糖苷酸)
  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：

  7,8-didehydro-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3-benzoate 、 (2S,3S,4S,5R)-6-Bromo-3,4,5-tris-isobutyryloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4 A molecular sieve 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-benzoyloxy-3-methyl-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：

  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

文献信息

• Selective synthesis of both isomers of morphine 6-β-d-glucuronide and their analogs
  作者：Igor Rukhman、Lev Yudovich、Gennadiy Nisnevich、Arie L Gutman

  DOI：10.1016/s0040-4020(00)01080-2

  日期：2001.2

  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.