(2S,3S,4R,5S)-3,4-dibenzoyloxy-2((1'S)-2'-benzoyloxy-1'-hydroxyethyl)-1-(2,2-diethoxycarbonylvinyl)-5-methoxypyrrolidine | 198640-99-2

• 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: (2S,3S,4R,5S)-3,4-dibenzoyloxy-2((1'S)-2'-benzoyloxy-1'-hydroxyethyl)-1-(2,2-diethoxycarbonylvinyl)-5-methoxypyrrolidine
• 英文别名: diethyl 2-[[(2S,3S,4R,5S)-3,4-dibenzoyloxy-2-[(1S)-2-benzoyloxy-1-hydroxyethyl]-5-methoxypyrrolidin-1-yl]methylidene]propanedioate
• CAS: 198640-99-2
• 化学式: C₃₆H₃₇NO₁₂
• 分子量: 675.689
• InChiKey: FZEGAMHBGSFFRA-NBCLCUQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S,3S,4R,5S)-3,4-dibenzoyloxy-2((1'S)-2'-benzoyloxy-1'-hydroxyethyl)-1-(2,2-diethoxycarbonylvinyl)-5-methoxypyrrolidine 在 吡啶 作用下， 反应 16.0h， 以71%的产率得到(2S,3S,4R,5S)-2((1'S)-1'-acetoxy-2'-benzoyloxyethyl)-3,4-dibenzoyloxy-1-(2,2-diethoxycarbonyl-vinyl)-5-methoxypyrrolidine
  参考文献：
  名称：

  Stereoselective syntheses of 4-amino-aldoses, and chiral pyrrolidine derivatives from glycosylenamines

  摘要：

  The stereocontrolled synthesis of N-protected 4-amino-4-deoxy-D-galacto- and -L-arabino-pyranoses starting from glycosylenamines via aza-anhydropyranoses is described. The steroselective transformation of the intermediate aza-anhydropyranoses into chiral pyrrolidines is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00404-7
• 作为产物：
  描述：

  2,3,6-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 在 吡啶 、 六甲基磷酰三胺 、 sodium methylate 、 lithium perchlorate 、 三氟乙酸 、 三氟乙酸酐 作用下， 反应 35.0h， 生成 (2S,3S,4R,5S)-3,4-dibenzoyloxy-2((1'S)-2'-benzoyloxy-1'-hydroxyethyl)-1-(2,2-diethoxycarbonylvinyl)-5-methoxypyrrolidine
  参考文献：
  名称：

  Stereoselective syntheses of 4-amino-aldoses, and chiral pyrrolidine derivatives from glycosylenamines

  摘要：

  The stereocontrolled synthesis of N-protected 4-amino-4-deoxy-D-galacto- and -L-arabino-pyranoses starting from glycosylenamines via aza-anhydropyranoses is described. The steroselective transformation of the intermediate aza-anhydropyranoses into chiral pyrrolidines is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00404-7

文献信息

• Stereoselective syntheses of 4-amino-aldoses, and chiral pyrrolidine derivatives from glycosylenamines
  作者：José Fuentes、David Olano、M.Angeles Pradera

  DOI：10.1016/s0957-4166(97)00404-7

  日期：1997.10

  The stereocontrolled synthesis of N-protected 4-amino-4-deoxy-D-galacto- and -L-arabino-pyranoses starting from glycosylenamines via aza-anhydropyranoses is described. The steroselective transformation of the intermediate aza-anhydropyranoses into chiral pyrrolidines is also reported. (C) 1997 Elsevier Science Ltd.