1-allyl-5-{2-[(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]ethyl}-4-([(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]methyl)pyridinium-3-olate | 937183-45-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-allyl-5-{2-[(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]ethyl}-4-([(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]methyl)pyridinium-3-olate
• 英文别名: 5-[2-[(3S,5S,6R)-4-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxo-5,6-diphenylmorpholin-3-yl]ethyl]-4-[[(3S,5S,6R)-4-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxo-5,6-diphenylmorpholin-3-yl]methyl]-1-prop-2-enylpyridin-1-ium-3-olate
• CAS: 937183-45-4
• 化学式: C₅₃H₅₇N₃O₉
• 分子量: 880.05
• InChiKey: BPCWGWHXTMRPFA-BCSRYQSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  65
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-allyl-5-{2-[(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]ethyl}-4-([(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]methyl)pyridinium-3-olate 在 四(三苯基膦)钯 硫代水杨酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.3h， 以87%的产率得到5-{2-[(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]ethyl}-4-([(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]methyl)-3-hydroxypyridine
  参考文献：
  名称：

  Practical Syntheses of Pyridinolines, Important Amino Acidic Biomarkers of Collagen Health

  摘要：

  The paper reports some successful results on the first fully stereoselective total synthesis of the collagen cross-link pyridinolines. All stereogenic centers are stereoselectively introduced using Williams glycine template methodology, and oxazinones are used as a source of chirality and as easily removable protecting groups of the amino acidic functionalities during the assembly of the pyridinoline nucleus.

  DOI：

  10.1021/jo070136g
• 作为产物：
  描述：

  tert-butyl (3S,5S,6R)-3-(4-iodo-3-oxobutyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate 、 丙烯胺 在 sodium carbonate 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 、 四氢呋喃 为溶剂， 反应 98.0h， 以27%的产率得到1-allyl-5-{2-[(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]ethyl}-4-([(3S,5S,6R)-4-(tert-butoxycarbonyl)-2-oxo-5,6-diphenylmorpholin-3-yl]methyl)pyridinium-3-olate
  参考文献：
  名称：

  Practical Syntheses of Pyridinolines, Important Amino Acidic Biomarkers of Collagen Health

  摘要：

  The paper reports some successful results on the first fully stereoselective total synthesis of the collagen cross-link pyridinolines. All stereogenic centers are stereoselectively introduced using Williams glycine template methodology, and oxazinones are used as a source of chirality and as easily removable protecting groups of the amino acidic functionalities during the assembly of the pyridinoline nucleus.

  DOI：

  10.1021/jo070136g