(2R,5S,6S)-5-[2-(benzyloxy)-1-hydroxyethyl]-2-(dimethoxycarbonylmethyl)-1-mesyl-2,5-dihydro-1H-pyrrole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,5S,6S)-5-[2-(benzyloxy)-1-hydroxyethyl]-2-(dimethoxycarbonylmethyl)-1-mesyl-2,5-dihydro-1H-pyrrole
• 英文别名: dimethyl 2-[(2R,5S)-5-[(1S)-1-hydroxy-2-phenylmethoxyethyl]-1-methylsulfonyl-2,5-dihydropyrrol-2-yl]propanedioate
• 化学式: C₁₉H₂₅NO₈S
• 分子量: 427.475
• InChiKey: AKOJWEZQTHMRET-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  6-O-benzyl-3-deoxy-3-N-(mesylamino)-4-O-mesyl-D-gulal 、 丙二酸二甲酯 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以48%的产率得到6-O-benzyl-3,4-dideoxy-4-(N-mesylamino)-3-(dimethoxycarbonylmethyl)-D-glucal
  参考文献：
  名称：

  Enantiopure Cis-2,5-Disubstituted 2,5-Dihydropyrroles from d-Glycal-Derived Vinyl Aziridines

  摘要：

  Upon treatment with the K- and Li-enolates of a methylene active compound, such as dimethyl malonate and dibenzoylmethane, D-allal- and c-galactal-derived vinyl N-mesyl aziridines are stereoselectively transformed, in a unique step, into diastereoisomeric, highly functionalized, enantiopure cis-2,5-disubstituted N-mesyl-2,5-dihydropyrroles.

  DOI：

  10.1021/ol402927s

文献信息

• Enantiopure <i>Cis</i>-2,5-Disubstituted 2,5-Dihydropyrroles from <scp>d</scp>-Glycal-Derived Vinyl Aziridines
  作者：Valeria Di Bussolo、Ileana Frau、Stefano Crotti、Gloria Uccello-Barretta、Federica Balzano、Mauro Pineschi、Paolo Crotti

  DOI：10.1021/ol402927s

  日期：2013.12.6

  Upon treatment with the K- and Li-enolates of a methylene active compound, such as dimethyl malonate and dibenzoylmethane, D-allal- and c-galactal-derived vinyl N-mesyl aziridines are stereoselectively transformed, in a unique step, into diastereoisomeric, highly functionalized, enantiopure cis-2,5-disubstituted N-mesyl-2,5-dihydropyrroles.