tert-butyl (3S,5S,6R)-3-[(R)-4-azido-3-(trimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate | 937183-41-0

• 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: tert-butyl (3S,5S,6R)-3-[(R)-4-azido-3-(trimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• 英文别名: tert-butyl (3S,5S,6R)-3-[(3R)-4-azido-3-trimethylsilyloxybutyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 937183-41-0
• 化学式: C₂₈H₃₈N₄O₅Si
• 分子量: 538.719
• InChiKey: PTWZVXPWGCGQQP-WSOYEBOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,5S,6R)-3-[(R)-4-azido-3-(trimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 22.0h， 生成 tert-butyl (3S,5S,6R)-3-[(3R)-4-[bis[4-[(3S,5S,6R)-4-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxo-5,6-diphenylmorpholin-3-yl]-2-oxobutyl]amino]-3-trimethylsilyloxybutyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
  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：

  三甲基氯硅烷 、 tert-butyl (3S,5S,6R)-3-[(3R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以90%的产率得到tert-butyl (3S,5S,6R)-3-[(R)-4-azido-3-(trimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
  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