5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-3-hydroxy-5-methoxy-6-methyl-2-[8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-2H-chromen-7-yloxy]-tetrahydro-pyran-4-yl ester | 265325-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-3-hydroxy-5-methoxy-6-methyl-2-[8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-2H-chromen-7-yloxy]-tetrahydro-pyran-4-yl ester
• CAS: 265325-07-3
• 化学式: C₃₀H₃₁NO₁₁S
• 分子量: 613.642
• InChiKey: VSHNSRXYUSHJSX-VCIRQRAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  163.59
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-4-tributylstannanyl-benzene 、 5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-3-hydroxy-5-methoxy-6-methyl-2-[8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-2H-chromen-7-yloxy]-tetrahydro-pyran-4-yl ester 在 palladium diacetate 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 以34%的产率得到5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-2-{4-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-8-methyl-2-oxo-2H-chromen-7-yloxy}-3-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Tosylates in palladium-catalysed coupling reactions. Application to the synthesis of arylcoumarin inhibitors of gyrase B

  摘要：

  The palladium-catalysed coupling reaction between tosylate derivatives and organostannanes has been investigated as a methodology for carbon-carbon bond formation. Aryl substituents have been successfully incorporated even in highly functionalised coumarin structures to afford new analogues of the antibiotic novobiocin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02351-5
• 作为产物：
  描述：

  4,7-dihydroxy-8-methyl-2H-1-benzopyran-2-one 在 吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-3-hydroxy-5-methoxy-6-methyl-2-[8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-2H-chromen-7-yloxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Tosylates in palladium-catalysed coupling reactions. Application to the synthesis of arylcoumarin inhibitors of gyrase B

  摘要：

  The palladium-catalysed coupling reaction between tosylate derivatives and organostannanes has been investigated as a methodology for carbon-carbon bond formation. Aryl substituents have been successfully incorporated even in highly functionalised coumarin structures to afford new analogues of the antibiotic novobiocin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02351-5