((1R,3S)-6,8-bis(benzyloxy)-5-iodo-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl 1-naphthoate | 1248682-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ((1R,3S)-6,8-bis(benzyloxy)-5-iodo-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl 1-naphthoate
• 英文别名: [(1R,3S)-5-iodo-1-methyl-2-(4-methylphenyl)sulfonyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isoquinolin-3-yl]methyl naphthalene-1-carboxylate
• CAS: 1248682-58-7
• 化学式: C₄₃H₃₈INO₆S
• 分子量: 823.748
• InChiKey: NILYPHJORWUQJR-HKFHRXRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-5-methoxy-7-((triisopropylsilyloxy)methyl)naphthalen-1-ylboronic acid 、 ((1R,3S)-6,8-bis(benzyloxy)-5-iodo-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl 1-naphthoate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium(II) iodide 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 以72%的产率得到((1R,3S,5R)-6,8-bis(benzyloxy)-5-(4-(benzyloxy)-5-methoxy-7-(((triisopropylsilyl)oxy)methyl)naphthalen-1-yl)-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl 1-naphthoate
  参考文献：
  名称：

  Total Synthesis of (+)-Korupensamine B via an Atropselective Intermolecular Biaryl Coupling

  摘要：

  The asymmetric total synthesis of nonracemic korupensamine B is reported. It includes a newly designed and highly trans-diastereoselective (>20:1 dr) route to the tetrahydroisoquinoline ring and an unprecedented atropdiastereoselective Suzuki-Miyaura coupling for construction of the fully fashioned naphthylisoquinoline framework that invokes pi stacking as a possible source of stereocontrol.

  DOI：

  10.1021/ja1065202
• 作为产物：
  描述：

  1-萘甲酸 、 ((1R,3S)-6,8-bis(benzyloxy)-5-iodo-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到((1R,3S)-6,8-bis(benzyloxy)-5-iodo-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl 1-naphthoate
  参考文献：
  名称：

  Total Synthesis of (+)-Korupensamine B via an Atropselective Intermolecular Biaryl Coupling

  摘要：

  The asymmetric total synthesis of nonracemic korupensamine B is reported. It includes a newly designed and highly trans-diastereoselective (>20:1 dr) route to the tetrahydroisoquinoline ring and an unprecedented atropdiastereoselective Suzuki-Miyaura coupling for construction of the fully fashioned naphthylisoquinoline framework that invokes pi stacking as a possible source of stereocontrol.

  DOI：

  10.1021/ja1065202