5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-2-[3-benzyloxycarbonyl-8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-2H-chromen-7-yloxy]-3-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester | 265325-08-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-2-[3-benzyloxycarbonyl-8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-2H-chromen-7-yloxy]-3-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester
• CAS: 265325-08-4
• 化学式: C₃₈H₃₇NO₁₃S
• 分子量: 747.777
• InChiKey: OKMMOQLKXYYSSW-RMVOVJEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  53.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  189.89
• 氢给体数：
  2.0
• 氢受体数：
  13.0

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)-2-[3-benzyloxycarbonyl-8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-2H-chromen-7-yloxy]-3-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester 在 四(三苯基膦)钯 lithium chloride 作用下， 以 1,4-二氧六环 为溶剂， 以46%的产率得到5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-2-{3-benzyloxycarbonyl-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 4-二甲氨基吡啶 、 potassium fluoride 、 氢氟酸 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 40.0h， 生成 5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-2-[3-benzyloxycarbonyl-8-methyl-2-oxo-4-(toluene-4-sulfonyloxy)-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