(R)-N-methyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium 2,3-dibenzoyl-L-tartarate | 104832-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (R)-N-methyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium 2,3-dibenzoyl-L-tartarate
• 英文别名: (R)-6,7-Dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (2R,3R)-2,3-bis(benzoyloxy)succinate；(2R,3R)-2,3-dibenzoyloxybutanedioic acid;(1R)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydro-1H-isoquinoline
• CAS: 104832-01-1
• 化学式: C₁₈H₁₄O₈*C₂₂H₂₉NO₅
• 分子量: 745.78
• InChiKey: LBGVOKZBYXHODD-YVGNGXOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (R)-N-methyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium 2,3-dibenzoyl-L-tartarate 在 sodium hydroxide 作用下， 以 水 为溶剂， 以94.8%的产率得到(R)-5'-methoxylaudanosine
  参考文献：
  名称：

  Two optimized synthetic pathways toward a chiral precursor of Mivacurium chloride and other skeletal muscle relaxants

  摘要：

  A chiral precursor of Mivacurium chloride, (R)-5'-methoxylaudanosine, was prepared using two different methods. The chiral resolution of racemic 5'-methoxylaudanosine, typically used in industry, was carried out in parallel with a procedure consisting of asymmetric transfer hydrogenation (ATH) and reductive methylation. A novel one-pot synthetic step was developed for the synthesis of racemic 5'-methoxylaudanosine. In both routes, the enantioselectivity was high but further purification was necessary to reach the level of a pharmaceutical standard. The individual synthetic steps reported herein can also be used for the synthesis of analogous bistetrahydroisoquinoline-based skeletal muscle relaxants. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.012
• 作为产物：
  描述：

  (7S)-1,2,3,10-四甲氧基-7-(甲基氨基)-6,7-二氢苯并[a]庚搭烯-9(5H)-酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.75h， 生成 (R)-N-methyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium 2,3-dibenzoyl-L-tartarate
  参考文献：
  名称：

  Two optimized synthetic pathways toward a chiral precursor of Mivacurium chloride and other skeletal muscle relaxants

  摘要：

  A chiral precursor of Mivacurium chloride, (R)-5'-methoxylaudanosine, was prepared using two different methods. The chiral resolution of racemic 5'-methoxylaudanosine, typically used in industry, was carried out in parallel with a procedure consisting of asymmetric transfer hydrogenation (ATH) and reductive methylation. A novel one-pot synthetic step was developed for the synthesis of racemic 5'-methoxylaudanosine. In both routes, the enantioselectivity was high but further purification was necessary to reach the level of a pharmaceutical standard. The individual synthetic steps reported herein can also be used for the synthesis of analogous bistetrahydroisoquinoline-based skeletal muscle relaxants. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.012

文献信息

• Two optimized synthetic pathways toward a chiral precursor of Mivacurium chloride and other skeletal muscle relaxants
  作者：Beáta Vilhanová、Václav Matoušek、Jiří Václavík、Kamila Syslová、Jan Přech、Jan Pecháček、Petr Šot、Jakub Januščák、Jaromír Toman、Jakub Zápal、Marek Kuzma、Petr Kačer

  DOI：10.1016/j.tetasy.2012.11.012

  日期：2013.1

  A chiral precursor of Mivacurium chloride, (R)-5'-methoxylaudanosine, was prepared using two different methods. The chiral resolution of racemic 5'-methoxylaudanosine, typically used in industry, was carried out in parallel with a procedure consisting of asymmetric transfer hydrogenation (ATH) and reductive methylation. A novel one-pot synthetic step was developed for the synthesis of racemic 5'-methoxylaudanosine. In both routes, the enantioselectivity was high but further purification was necessary to reach the level of a pharmaceutical standard. The individual synthetic steps reported herein can also be used for the synthesis of analogous bistetrahydroisoquinoline-based skeletal muscle relaxants. (C) 2012 Elsevier Ltd. All rights reserved.